Microbiocidal oxadiazole derivatives

ABSTRACT

Compounds of the formula (I) wherein the substituents are as defined in claim  1 , useful as a pesticides and especially as fungicides.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a 371 National Stage application of InternationalApplication No. PCT/EP2016/057845, filed Apr. 8, 2016, the entirecontents of which applications are hereby incorporated by reference.

The present invention relates to microbiocidal oxadiazole derivatives,e.g., as active ingredients, which have microbiocidal activity, inparticular fungicidal activity. The invention also relates toagrochemical compositions which comprise at least one of the oxadiazolederivatives, to the preparation of these compositions and to the use ofthe oxadiazole derivatives or compositions in agriculture orhorticulture for controlling or preventing infestation of plants,harvested food crops, seeds or non-living materials by phytopathogenicmicroorganisms, in particular, fungi.

Phenyl oxadiazole derivatives are known as pharmaceutically-activeagents from, eg, WO 2013/008162. WO 2015/185485 discloses the use ofsubstituted oxadiazoles for combating phytopathogenic fungi.

According to the invention, there is provided a compound of formula (I):

wherein

R¹ is hydrogen;

R² is halogen, methyl or methoxy;

R³ represents hydrogen or C₁₋₄alkyl; and

R⁴ represents R^(4A), R^(4B), R^(4C), R^(4D) or R^(4E); wherein

R^(4A) represents heterocyclylC₀₋₆alkyl wherein the heterocyclyl moietyis a 5- or 6-membered non-aromatic ring which comprises 1, 2 or 3heteroatoms individually selected from N, O and S, optionallysubstituted by 1, 2 or 3 substitutents, which may be the same ordifferent, selected from R^(5A);

R^(5A) represents C₁₋₄alkyl, C₁₋₄alkoxy, C₁₋₄alkoxycarbonyl,phenylC₀₋₂alkyl;

R^(4B) represents C₃₋₈cycloalkylC₀₋₆alkyl optionally substituted by 1,2, 3 or 4 substitutents, which may be the same or different, selectedfrom R^(5B);

R^(5B) represents cyano, halogen, C₁₋₄alkyl, C₂₋₄alkynyl,C₁₋₄alkoxycarbonyl, C₃₋₆cycloalkylC₀₋₂alkyl, phenylC₀₋₂alkyl, andwherein any of said cycloalkyl or phenyl moieties are optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R^(6B); and

R^(6B) represents methyl, methoxy or halogen;

R^(4C) represents C₁₋₆alkyl, C₂₋₆alkenyl or C₂₋₆alkynyl, whereinC₁₋₆alkyl is optionally substituted by 1, 2 or 3 substituents, which maybe the same or different, selected from R^(5C);

R^(5C) represents halogen, C₁₋₄alkoxy, C₁₋₄alkylcarbonyl,C₁₋₄alkoxycarbonyl, hydroxyl, C₁₋₄alkylaminocarbonyl;

R^(4D) represents a phenylC₀₋₆alkyl optionally substituted by 1, 2, 3, 4or 5 substitutents, which may be the same or different, selected fromR^(5D);

R^(5D) represents cyano, halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl,C₂₋₄alkynyl, haloC₁₋₄alkyl, C₁₋₄alkoxy, C₁₋₄alkylcarbonyl,C₁₋₄alkoxycarbonyl, aminocarbonyl, C₁₋₄alkylaminocarbonyl,diC₁₋₄alkylaminocarbonyl, C₁₋₄alkoxycarbonylamino,C₃₋₈cycloalkylC₀₋₆alkyl, phenylC₀₋₆alkyl, heteroarylC₀₋₆alkyl whereinthe heteroaryl moiety is a 5- or 6-membered aromatic ring whichcomprises 1, 2, 3 or 4 heteroatoms individually selected from N, O andS, heterocyclylC₀₋₆alkyl wherein the heterocyclyl moiety is a 5- or6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, and wherein any of saidcycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionallysubstituted by 1, 2, 3, 4 or 5 substituents, which may be the same ordifferent, selected from R^(6D); and

R^(6D) represents methyl, methoxy or halogen; and

R^(4E) represents heteroarylC₀₋₆alkyl wherein the heteroaryl moiety is a5- or 6-membered aromatic ring comprising 1, 2, 3 or 4 heteroatomsindividually selected from N, O and S, and wherein theheteroarylC₀₋₆alkyl moiety is optionally substituted by 1, 2, 3, 4 or 5substitutents, which may be the same or different, selected from R^(5E);

R^(5E) represents cyano, amino, halogen, hydroxy, C₁₋₄alkyl,C₂₋₄alkenyl, C₂₋₄alkynyl, haloC₁₋₄alkyl, C₁₋₄alkoxy, C₁₋₄alkylamino,diC₁₋₄alkylamino, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, aminocarbonyl,C₁₋₄alkylaminocarbonyl, diC₁₋₄alkylaminocarbonyl,C₁₋₄alkoxycarbonylamino, C₃₋₈cycloalkylC₀₋₆alkyl, phenylC₀₋₆alkyl,heteroarylC₀₋₆alkyl wherein the heteroaryl moiety is a 5- or 6-memberedaromatic ring which comprises 1, 2, 3 or 4 heteroatoms individuallyselected from N, O and S, heterocyclylC₀₋₆alkyl wherein the heterocyclylmoiety is a 5- or 6-membered non-aromatic ring which comprises 1, 2 or 3heteroatoms individually selected from N, O and S, and wherein any ofsaid cycloalkyl, phenyl, heteroaryl and heterocyclyl are optionallysubstituted by 1, 2, 3, 4 or 5 substitutents, which may be the same ordifferent, selected from R^(6E); and

R^(6E) represents methyl, methoxy or halogen;

or a salt or an N-oxide thereof; wherein

when R⁴ is R^(4A), the compound according to Formula (I) is not:

-   2-fluoro-N-(pyrrolidin-3-yl)-4-[(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)]benzamide,-   2-fluoro-N-(1-(pyrrolidin-1-yl)propan-2-yl)-4-[(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)]benzamide,-   2-fluoro-N-(1-(piperidin-1-yl)propan-2-yl)-4-[(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)]benzamide,-   2-fluoro-N-(1-morpholinopropan-2-yl)-4-[(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)]benzamide,    or-   2-fluoro-N-(4-methoxypyrrolidin-3-yl)-4-[(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)]benzamide;

when R⁴ is R^(4C), the compound according to Formula (I) is not:

-   2-fluoro-N-(1-hydroxypropan-2-yl)-4-[(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)]benzamide;    and

when R⁴ is R^(4E), the compound according to Formula (I) is not:

-   N-(2,6-dimethylpyridin-4-yl)-2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide.

Surprisingly, it has been found that the novel compounds of formula (I)have, for practical purposes, a very advantageous level of biologicalactivity for protecting plants against diseases that are caused byfungi.

According to the invention, there is provided an agrochemicalcomposition comprising a fungicidally effective amount of a compound offormula (I) optionally, further comprising at least one additionalactive ingredient and/or an agrochemically-acceptable diluent orcarrier.

According to the invention, there is provided method of controlling orpreventing infestation of useful plants by phytopathogenicmicroorganisms, wherein a fungicidally effective amount of a compound offormula (I), or a composition comprising this compound as activeingredient, is applied to the plants, to parts thereof or the locusthereof.

According to the invention, there is provided the use of a compound offormula (I) as a fungicide.

Where substituents are indicated as being optionally substituted, thismeans that they may or may not carry one or more identical or differentsubstituents.

Cyano refers to a —CN group.

Hydroxy refers to a —OH group

Halogen (halo) refers to fluorine, chlorine, bromine or iodine.

Amino refers to an —NH₂ group.

As used herein, the term “C₁₋₆alkyl” refers to a straight or branchedhydrocarbon chain radical consisting solely of carbon and hydrogenatoms, containing no unsaturation, having from one to six carbon atoms,and which is attached to the rest of the molecule by a single bond. Theterm “C₁₋₄alkyl” is to be construed accordingly. Examples of C₁₋₆alkylinclude, but are not limited to, methyl, ethyl, n-propyl, 1-methylethyl(iso-propyl), n-butyl, n-pentyl and 1,1-dimethylethyl (t-butyl).

As used herein, the term “C₂₋₆alkenyl” refers to a straight or branchedhydrocarbon chain radical group consisting solely of carbon and hydrogenatoms, containing at least one double bond that can be of either the(E)- or (Z)-configuration, having from two to six carbon atoms, which isattached to the rest of the molecule by a single bond. The term“C₂₋₄alkenyl” is to be construed accordingly. Examples of C₂₋₆alkenylinclude, but are not limited to, ethenyl, prop-1-enyl, but-1-enyl.

As used herein, the term “C₂₋₆alkynyl” refers to a straight or branchedhydrocarbon chain radical group consisting solely of carbon and hydrogenatoms, containing at least one triple bond, having from two to sixcarbon atoms, and which is attached to the rest of the molecule by asingle bond. The term “C₂₋₄alkynyl” is to be construed accordingly.Examples of C₂₋₆alkynyl include, but are not limited to, ethynyl,prop-1-ynyl, but-1-ynyl.

As used herein, the term “haloC₁₋₄alkyl” refers to a C₁₋₄alkyl radical,as defined above, substituted by one or more halo radicals, as definedabove. Examples of haloC₁₋₄alkyl include, but are not limited to,trifluoromethyl, difluoromethyl, fluoromethyl, trichloromethyl,2,2,2-trifluoroethyl, 1-fluoromethyl-2-fluoroethyl,3-bromo-2-fluoropropyl and 1-bromomethyl-2-bromoethyl.

As used herein, the term “C₁₋₄alkoxy” refers to a radical of the formula—OR_(a) where R_(a) is a C₁₋₄alkyl radical as generally defined above.Examples of C₁₋₄alkoxy include, but are not limited to, methoxy, ethoxy,propoxy, iso-propoxy, n-butoxy.

As used herein, the term “C₁₋₄alkylamino” refers to a radical of theformula —NH—R_(a) where R_(a) is a C₁₋₄alkyl radical as defined above.

As used herein, the term “di-C₁₋₄alkylamino” refers to a radical of theformula —N(R_(a))(R_(b)) where R_(a) and R_(b) independently can be thesame or a different C₁₋₄alkyl radical as defined above.

As used herein, the term “C₁₋₄alkylcarbonyl” refers to a radical of theformula —C(O)—R_(a) where R_(a) is a C₁₋₄alkyl radical as defined above.

As used herein, the term “C₁₋₄alkoxycarbonyl” refers to a radical of theformula —C(O)—O—R_(a) where R_(a) is a C₁₋₄alkyl radical as definedabove.

As used herein, the term “C₁₋₄alkoxycarbonylamino” refers to a radicalof the formula —NH—C(O)—O—R_(a) where R_(a) is a C₁₋₄alkyl radical asdefined above.

As used herein, the term “aminocarbonyl” refers to a radical of theformula —C(O)—NH₂.

As used herein, the term “C₁₋₄alkylaminocarbonyl” refers to a radical ofthe formula —C(O)—NH—R_(a) where R_(a) is a C₁₋₄alkyl radical as definedabove.

As used herein, the term “diC₁₋₄alkylaminocarbonyl” refers to a radicalof the formula —C(O)—N(R_(a))—R_(a) where each R_(a) is a C₁₋₄alkylradical, which may be the same or different, as defined above.

As used herein, the term “C₃₋₈cycloalkylC₀₋₆alkyl” refers to a stable,non-aromatic, monocyclic hydrocarbon radical consisting solely of carbonand hydrogen atoms, the cycloalkyl group having from three to eightcarbon atoms, and which is saturated or partially unsaturated andattached to the rest of the molecule by a single bond or by a C₁₋₆alkylradical as defined above. The terms “C₃₋₆cycloalkylC₀₋₂alkyl” and“C₃₋₄cycloalkylC₀₋₂alkyl” are to be construed accordingly. Examples ofC₃₋₈cycloalkylC₀₋₆alkyl include, but are not limited to, cyclopropyl,cyclopropyl-methyl, cyclobutyl, cyclobutyl-ethyl, cyclopentyl,cyclopentyl-propyl, cyclohexyl, cyclohepty and cyclooctyl.

As used herein, the term “phenylC₀₋₆alkyl” refers to a phenyl ringattached to the rest of the molecule by a single bond or by a C₁₋₆alkylradical as defined above. The term “phenylC₀₋₂alkyl” should be construedaccordingly. Examples of phenylC₀₋₆alkyl include, but are not limitedto, phenyl and benzyl.

As used herein, the term “heterocyclyl” or “heterocyclic” refers to astable 5- or 6-membered non-aromatic monocyclic ring radical whichcomprises 1, 2, or 3, heteroatoms individually selected from nitrogen,oxygen and sulfur. The heterocyclyl radical may be bonded to the rest ofthe molecule via a carbon atom or heteroatom. Examples of heterocyclylinclude, but are not limited to pyrrolinyl, pyrrolidyl, tetrahydrofuryl,tetrahydrothienyl, piperidyl, piperazinyl, tetrahydropyranyl,morpholinyl or perhydroazepinyl.

As used herein, the term “heterocyclylC₀₋₆alkyl” refers to aheterocyclic ring as defined above which is attached to the rest of themolecule by a single bond or by a C₁₋₆alkyl radical as defined above.The term “heterocyclylC₀₋₂alkyl” should be construed accordingly.

As used herein, the term “heteroaryl” refers to a 5- or 6-memberedaromatic monocyclic ring radical which comprises 1, 2, 3 or 4heteroatoms individually selected from nitrogen, oxygen and sulfur. Theheteroaryl radical may be bonded to the rest of the molecule via acarbon atom or heteroatom. Examples of heteroaryl include, but are notlimited to, furyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl,isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl,triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl or pyridyl.

As used herein, the term “heteroarylC₀₋₆alkyl” refers to a heteroarylring as defined above which is attached to the rest of the molecule by asingle bond or by a C₁₋₆alkyl radical as defined above. Likewise, theterms “heteroarylC₀₋₂alkyl” and “heteroarylC₀₋₁alkyl” are to beconstrued accordingly.

The presence of one or more possible asymmetric carbon atoms in acompound of formula (I) means that the compounds may occur in opticallyisomeric forms, i.e., enantiomeric or diastereomeric forms. Alsoatropisomers may occur as a result of restricted rotation about a singlebond. Formula (I) is intended to include all those possible isomericforms and mixtures thereof. The present invention includes all thosepossible isomeric forms and mixtures thereof for a compound of Formula(I). Likewise, Formula (I) is intended to include all possibletautomers. The present invention includes all possible tautomeric formsfor a compound of Formula (I).

In each case, the compounds of Formula (I) according to the inventionare in free form, in oxidized form as an N-oxide, in covalently hydratedform, or in salt form, e.g., an agrochemically acceptable salt form.

N-oxides are oxidized forms of tertiary amines or oxidized forms ofnitrogen containing heteroaromatic compounds. They are described forinstance in the book “Heterocyclic N-oxides” by A. Albini and S. Pietra,CRC Press, Boca Raton 1991.

The following list provides definitions, including preferreddefinitions, for substituents R¹, R², R³, R⁴ (ie, R^(4A), R^(4B),R^(4C), R^(4D), R^(4E)), R⁵ (ie, R^(5A), R^(5B), R^(5C), R^(5D), R^(5E))and R⁶ (ie, R^(6B), R^(6D), R^(6E)) with reference to compounds offormula (I). For any one of these substituents, any of the definitionsgiven below may be combined with any definition of any other substituentgiven below or elsewhere in this document.

R¹ is hydrogen.

R² is halogen, methyl or methoxy. Preferably, R² is halogen. Morepreferably, R² is chlorine or fluorine. Most preferably, R² is fluorine.

R³ represents hydrogen or C₁₋₄alkyl. Preferably, R³ is hydrogen ormethyl. Most preferably, R³ is hydrogen.

R⁴ represents R^(4A), R^(4B), R^(4C), R^(4D) or R^(4E).

In one embodiment of the invention, R⁴ is R^(4A). In another embodimentof the invention, R⁴ is R^(4B). In another embodiment of the invention,R⁴ is R^(4C). In another embodiment of the invention, R⁴ is R^(4D). Inanother embodiment of the invention, R⁴ is R^(4E).

R^(4A) represents heterocyclylC₀₋₆alkyl wherein the heterocyclyl moietyis a 5- or 6-membered non-aromatic ring which comprises 1, 2 or 3heteroatoms individually selected from N, O and S, optionallysubstituted by 1, 2 or 3 substitutents, which may be the same ordifferent, selected from R^(5A).

Preferably, R^(4A) represents heterocyclylC₀₋₂alkyl wherein theheterocyclyl moiety is a 5- or 6-membered non-aromatic ring whichcomprises 1, 2 or 3 heteroatoms individually selected from N, O and S,and wherein the heterocyclylC₀₋₂alkyl moiety is optionally substitutedby 1 or 2 substitutents, which may be the same or different, selectedfrom R^(5A). More preferably, R^(4A) represents heterocyclylC₀₋₁alkylwherein the heterocyclyl moiety is a 5- or 6-membered non-aromatic ringwhich comprises 1 or 2 heteroatoms individually selected from N, O andS, and wherein the heterocyclylC₀₋₁alkyl moiety is optionallysubstituted by 1 or 2 substitutents, which may be the same or different,selected from R^(5A). Even more preferably, R^(4A) representsheterocyclylC₀₋₁alkyl wherein the heterocyclyl moiety is a 5- or6-membered non-aromatic ring which comprises 1 or 2 heteroatomsindividually selected from N and O, and wherein theheterocyclylC₀₋₁alkyl moiety is optionally substituted by 1substitutent, selected from R^(5A).

In certain embodiments, R^(4A) may be a pyrrolidinyl, piperidinyl,(pyrrolidinyl)methyl, (piperidinyl)methyl, tetrahydrofuranyl,tetrahydropyranyl, 1,4-dioxanyl, (tetrahydrofuranyl)methyl,(tetrahydropyranyl)methyl, (1,4-dioxanyl)methyl, 1,3-dioxolanyl,(1,3-dioxolanyl)methyl, tetrahydrothienyl, tetrahydropyranyl,(tetrahydrothienyl)methyl or (tetrahydropyranyl)methyl, which isoptionally substituted by 1 or 2 substitutents, which may be the same ordifferent, selected from R^(5A).

R^(4B) represents C₃₋₈cycloalkylC₀₋₆alkyl optionally substituted by 1,2, 3 or 4 substitutents, which may be the same or different, selectedfrom R^(5B).

Preferably, R^(4B) represents C₃₋₆cycloalkylC₀₋₂alkyl optionallysubstituted by 1 or 2 substitutents, which may be the same or different,selected from R^(5B). More preferably, R^(4B) representsC₃₋₄cycloalkylC₀₋₂alkyl optionally substituted by 1 or 2 substitutents,which may be the same or different, selected from R^(5B). Preferably,R^(4B) is cyclopropyl, (cyclopropyl)methyl, 1-(cyclopropyl)ethyl,cyclobutyl, (cyclobutyl)methyl, cyclopentyl, (cyclopentyl)methyl,cyclohexyl, 1-(cyclohexyl)ethyl or cyclooctyl, optionally substituted by1 or 2 substitutents, which may be the same or different, selected fromR^(5B).

R^(4C) represents C₁₋₆alkyl, C₂₋₆alkenyl or C₂₋₆alkynyl, whereinC₁₋₆alkyl is optionally substituted by 1, 2 or 3 substituents, which maybe the same or different, selected from R^(5C).

Preferably, R^(4C) represents C₁₋₆alkyl, C₂₋₆alkenyl or C₂₋₆alkynyl,wherein C₁₋₆alkyl is optionally substituted by 1 or 2 substituents whichmay be the same or different, selected from R^(5C), wherein R^(5C)represents C₁₋₄alkoxy or hydroxyl. More preferably, R^(4C) representsC₁₋₆alkyl, C₂₋₆alkenyl or C₂₋₆alkynyl, wherein C₁₋₆alkyl is optionallysubstituted by 1 substituent selected from R^(5C), wherein R^(5C)represents C₁₋₄alkoxy or hydroxyl. Even more preferably, R^(4C)represents C₁₋₆alkyl optionally substituted by 1 substituent selectedfrom R^(5C), wherein R^(5C) represents hydroxyl; or R^(4C) representsC₂₋₆alkenyl or C₂₋₆alkynyl.

R^(4D) represents a phenylC₀₋₆alkyl optionally substituted by 1, 2, 3, 4or 5 substitutents, which may be the same or different, selected fromR^(5D).

Preferably, R^(4D) represents phenylC₀₋₆alkyl optionally substituted by1 or 2 substitutents, which may be the same or different, selected fromR^(5D). More preferably, R^(4D) represents phenylC₀₋₂alkyl optionallysubstituted by 1 or 2 substitutents, which may be the same or different,selected from R^(5D).

R^(4E) represents heteroarylC₀₋₆alkyl wherein the heteroaryl moiety is a5- or 6-membered aromatic ring comprising 1, 2, 3 or 4 heteroatomsindividually selected from N, O and S, and wherein theheteroarylC₀₋₆alkyl moiety is optionally substituted by 1, 2, 3, 4 or 5substitutents, which may be the same or different, selected from R^(5E).

Preferably, R^(4E) represents heteroarylC₀₋₂alkyl wherein the heteroarylmoiety is a 5- or 6-membered aromatic ring comprising 1, 2 or 3heteroatoms individually selected from N, O and S, and wherein theheteroarylC₀₋₂alkyl moiety is optionally substituted by 1 or 2substituents, which may be the same or different, selected from R^(5E).More preferably, R^(4E) represents heteroarylC₀₋₂alkyl, wherein theheteroaryl moiety of R^(4E) is a 5-membered aromatic ring comprising 1or 2 heteroatoms individually selected from N, O and S, and wherein theheteroarylC₀₋₂alkyl moiety is optionally substituted by 1 or 2substitutents, which may be the same or different, selected from R^(5E).In some embodiments of the invention, R^(4E) comprises at least oneheteroatom which is sulfur, such as a thienyl moiety, in particular, a2-thienyl moiety. In some embodiments of the invention, R^(4E) may bepyridinyl, pyrazolyl, furanyl, triazolyl, imidazolyl, thiazolyl. In someembodiments of the invention, R^(4E) is unsubstituted.

R^(5A) represents C₁₋₄alkyl, C₁₋₄alkoxy, C₁₋₄alkoxycarbonyl,phenylC₀₋₂alkyl. Preferably, R^(5A) represents methyl, methoxy,methoxycarbonyl, tert-butyloyxcarbonyl or benzyl.

R^(5B) represents cyano, halogen, C₁₋₄alkyl, C₂₋₄alkynyl,C₁₋₄alkoxycarbonyl, C₃₋₆cycloalkylC₀₋₂alkyl, phenylC₀₋₂alkyl, andwherein any of said cycloalkyl or phenyl moieties is optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R^(6B).

Preferably, R^(5B) represents cyano, fluoro, methyl, ethynyl,cyclopropyl, phenyl or benzyl, wherein cyclopropyl and phenyl moietiesare optionally substituted by 1, 2 or 3 substituents, which may be thesame or different, selected from R^(6B).

R^(5C) represents halogen, C₁₋₄alkoxy, C₁₋₄alkylcarbonyl,C₁₋₄alkoxycarbonyl, hydroxyl, C₁₋₄alkylaminocarbonyl. In certainembodiments, R^(5C) may also be haloC₁₋₄alkoxy.

R^(5D) represents cyano, halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl,C₂₋₄alkynyl, haloC₁₋₄alkyl, C₁₋₄alkoxy, C₁₋₄alkylcarbonyl,C₁₋₄alkoxycarbonyl, aminocarbonyl, C₁₋₄alkylaminocarbonyl,diC₁₋₄alkylaminocarbonyl, C₁₋₄alkoxycarbonylamino,C₃₋₈cycloalkylC₀₋₆alkyl, phenylC₀₋₆alkyl, heteroarylC₀₋₆alkyl whereinthe heteroaryl moiety is a 5- or 6-membered aromatic ring whichcomprises 1, 2, 3 or 4 heteroatoms individually selected from N, O andS, heterocyclylC₀₋₆alkyl wherein the heterocyclyl moiety is a 5- or6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, and wherein any of saidcycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionallysubstituted by 1, 2, 3, 4 or 5 substituents, which may be the same ordifferent, selected from R^(6D).

Preferably, R^(5D) represents halogen, C₁₋₄alkyl, haloC₁₋₄alkyl,C₁₋₄alkoxy, C₃₋₈cycloalkylC₀₋₆alkyl, phenylC₀₋₆alkyl,heteroarylC₀₋₆alkyl wherein the heteroaryl moiety is a 5- or 6-memberedaromatic ring which comprises 1, 2, 3 or 4 heteroatoms individuallyselected from N, O and S, heterocyclylC₀₋₆alkyl wherein the heterocyclylmoiety is a 5- or 6-membered non-aromatic ring which comprises 1, 2 or 3heteroatoms individually selected from N, O and S. More preferably,R^(5D) represents halogen, C₁₋₄alkyl, haloC₁₋₄alkyl, C₁₋₄alkoxy orheterocyclylC₀₋₆alkyl wherein the heterocyclyl moiety is a 5- or6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S. Even more preferably, R^(5D) isselected from fluoro, chloro, methoxy, methyl, ethyl, trifluoromethyland N-morpholinyl, in particular, when there are 1 or 2 R^(5D)substitutents, which may be the same or different, these are phenyl ringsubstituents.

R^(5E) represents cyano, amino, halogen, hydroxy, C₁₋₄alkyl,C₂₋₄alkenyl, C₂₋₄alkynyl, haloC₁₋₄alkyl, C₁₋₄alkoxy, C₁₋₄alkylamino,diC₁₋₄alkylamino, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, aminocarbonyl,C₁₋₄alkylaminocarbonyl, diC₁₋₄alkylaminocarbonyl,C₁₋₄alkoxycarbonylamino, C₃₋₈cycloalkylC₀₋₆alkyl, phenylC₀₋₆alkyl,heteroarylC₀₋₆alkyl wherein the heteroaryl moiety is a 5- or 6-memberedaromatic ring which comprises 1, 2, 3 or 4 heteroatoms individuallyselected from N, O and S, heterocyclylC₀₋₆alkyl wherein the heterocyclylmoiety is a 5- or 6-membered non-aromatic ring which comprises 1, 2 or 3heteroatoms individually selected from N, O and S, and wherein any ofsaid cycloalkyl, phenyl, heteroaryl and heterocyclyl is optionallysubstituted by 1, 2, 3, 4 or 5 substitutents, which may be the same ordifferent, selected from R^(6E).

Preferably, R^(5E) represents amino, cyano, halogen, hydroxy, C₁₋₄alkyl,C₂₋₃alkenyl, C₂₋₃alkynyl, haloC₁₋₂alkyl, C₁₋₂alkoxy, C₁₋₂alkylcarbonyl,C₁₋₂alkoxycarbonyl, aminocarbonyl, C₁₋₂alkylaminocarbonyl,diC₁₋₂alkylaminocarbonyl, C₁₋₂alkoxycarbonylamino,C₃₋₈cycloalkylC₀₋₂alkyl, phenylC₀₋₂alkyl, heteroarylC₀₋₂alkyl whereinthe heteroaryl moiety is a 5- or 6-membered aromatic ring whichcomprises 1, 2, 3 or 4 heteroatoms individually selected from N, O andS, heterocyclylC₀₋₂alkyl wherein the heterocyclyl moiety is a 5- or6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, and wherein any of saidcycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionallysubstituted by 1, 2, 3, 4 or 5 substituents, which may be the same ordifferent, selected from R^(6E). More preferably, R^(5E) representsamino, cyano, halogen, C₁₋₄alkyl, haloC₁₋₂alkyl, C₁₋₂alkoxy,C₁₋₂alkylcarbonyl, C₁₋₂alkoxycarbonyl, aminocarbonyl,C₁₋₂alkylaminocarbonyl, diC₁₋₂alkylaminocarbonyl,C₁₋₂alkoxycarbonylamino, C₃₋₈cycloalkylC₀₋₂alkyl wherein any of saidmoieties is optionally substituted by 1, 2, or 3 substituents, which maybe the same or different, selected from R^(6E). Even more preferably,R^(5E) represents amino, cyano, halogen, C₁₋₄alkyl, haloC₁₋₂alkyl,C₁₋₂alkoxy, aminocarbonyl, wherein any of said moieties are optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R^(6E). Most preferably, R^(5E) is selectedfrom amino, cyano, halogen, C₁₋₄alkyl, haloC₁₋₂alkyl or C₁₋₂alkoxy.

R^(6B) represents methyl, methoxy or halogen. Preferably, R^(6B)represents chloro.

R^(6D) represents methyl, methoxy or halogen. Preferably, R⁶ representsmethyl, methoxy, fluoro or chloro.

R^(6E) represents methyl, methoxy or halogen. Preferably, R^(6E)represents methyl, methoxy, fluoro or chloro.

Preferably, R¹ is hydrogen and R² is fluoro;

-   -   R³ represents hydrogen, methyl, ethyl or n-propyl; and    -   R⁴ is R^(4A) and represents pyrrolidinyl, piperidinyl,        (pyrrolidinyl)methyl, (piperidinyl)methyl, tetrahydrofuranyl,        (tetrahydrofuranyl)methyl, (tetrahydropyranyl)methyl,        (1,4-dioxanyl)methyl, (1,3-dioxolanyl)methyl, tetrahydrothienyl        or tetrahydrothiopyranyl optionally substituted by 1 or 2        substituents which may be the same or different, selected from        R^(5A), wherein R^(5A) is selected from methyl, methoxy,        methoxycarbonyl or tert-butyloxycarbonyl.

Preferably, R¹ is hydrogen and R² is halogen (preferably fluorine);

-   -   R³ is hydrogen; and    -   R⁴ is R^(4B) and represents cyclopropyl, (cyclopropyl)methyl,        1-(cyclopropyl)ethyl, cyclobutyl, (cyclobutyl)methyl,        cyclopentyl, (cyclopentyl)methyl, cyclohexyl,        1-(cyclohexyl)ethyl or cyclooctyl, optionally substituted by 1        or 2 substitutents, which may be the same or different, selected        from R^(5B), wherein R^(5B) represents cyano, fluoro, methyl,        ethynyl, cyclopropyl, phenyl or benzyl, wherein the cyclopropyl        and phenyl moieties are optionally substituted by 1 substituent        selected from R^(6B), wherein R^(6B) is chloro.

Preferably, R¹ is hydrogen and R² is halogen;

-   -   R³ represents hydrogen, methyl or ethyl; and    -   R⁴ is R^(4C) and represents C₂₋₆alkenyl, C₂₋₆alkynyl or        C₁₋₆alkyl optionally substituted by 1 or 2 substituents which        may be the same or different, selected from R^(5C), wherein        R^(5C) represents C₁₋₄alkoxy or hydroxyl.

Even more preferably, R¹ is hydrogen and R² is fluorine;

-   -   R³ represents hydrogen or methyl; and    -   R⁴ is R^(4C) and represents C₂₋₆alkenyl, C₂₋₆alkynyl or        C₁₋₆alkyl optionally substituted by 1 substituent selected from        R^(5C), wherein R^(5C) represents C₁₋₄alkoxy or hydroxyl.

Still further preferably, R¹ is hydrogen and R² is fluorine;

-   -   R³ is hydrogen; and    -   R⁴ is R^(4C) and represents C₂₋₆alkenyl, C₂₋₆alkynyl or        C₁₋₆alkyl optionally substituted by 1 substituent selected from        R^(5C), wherein R^(5C) represents C₁₋₄alkoxy or hydroxyl.

Preferably, R¹ is hydrogen and and R² is fluoro;

-   -   R³ represents hydrogen or methyl;    -   R⁴ is R^(4D) and represents a phenylC₀₋₁alkyl optionally        substituted by 1, 2, 3, 4 or 5 substituents, which may be the        same or different, selected from R^(5D).

More preferably, R¹ is hydrogen and and R² is fluoro;

-   -   R³ represents hydrogen or methyl;    -   R⁴ is R^(4D) and represents a phenylC₀₋₁alkyl optionally        substituted by 1, 2 or 3 substituents, which may be the same or        different, selected from R^(5D).

Preferably, R¹ is hydrogen and and R² is fluoro;

-   -   R³ represents hydrogen; and    -   R⁴ is R^(4E) and represents a heteroarylC₀₋₁alkyl wherein the        heteroaryl moiety is a 5- or 6-membered aromatic ring comprising        1, 2 or 3 heteroatoms individually selected from N, O and S, and        wherein the heteroarylC₀₋₁alkyl moiety is optionally substituted        by 1 or 2 substituents, which may be the same or different,        selected from R^(5E), wherein R^(5E) is selected from amino,        cyano, halogen, C₁₋₄alkyl, haloC₁₋₂alkyl or C₁₋₂alkoxy.

Also, in accordance with this disclosure, there is provided a method ofcontrolling or preventing infestation of a useful plant byphytopathogenic microorganisms, which comprises applying to the plant,to a part thereof or the locus thereof, a fungicidally effective amountof a compound of formula (I):

wherein

R¹ and R² independently represent hydrogen, halogen, methyl or methoxy;

R³ represents hydrogen or C₁₋₄alkyl;

R⁴ represents C₁₋₆alkyl, C₂₋₆alkenyl, C₂₋₆alkynyl, halogenC₁₋₆alkyl,C₁₋₆alkoxy, C₁₋₆alkoxyC₁₋₆alkyl, C₁₋₆alkylcarbonylC₁₋₆alkyl,C₁₋₆alkoxycarbonylC₁₋₆alkyl, hydroxylC₁₋₆alkyl, aminoC₁₋₆alkyl,C₁₋₄alkylaminoC₁₋₆alkyl, diC₁₋₄alkylaminoC₁₋₆alkyl,aminocarbonylC₁₋₆alkyl, C₁₋₄alkylaminocarbonylC₁₋₆alkyl,diC₁₋₄alkylaminocarbonylC₁₋₆alkyl, C₃₋₈cycloalkylC₀₋₆alkyl,phenylC₀₋₆alkyl, phenylC₀₋₆alkylaminoC₁₋₆alkyl,phenylC₀₋₆alkylamino(C₁₋₄alkyl)C₁₋₆alkyl, heteroarylC₀₋₆alkyl whereinthe heteroaryl moiety is a 5- or 6-membered aromatic ring whichcomprises 1, 2, 3 or 4 heteroatoms individually selected from N, O andS, heterocyclylC₀₋₆alkyl wherein the heterocyclyl moiety is a 5- or6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, and wherein any of saidcycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionallysubstituted by 1, 2, 3, 4 or 5 substituents, which may be the same ordifferent, selected from R⁵;

R⁵ represents cyano, amino, halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl,C₂₋₄alkynyl, halogenC₁₋₄ alkyl, C₁₋₄alkoxy, C₁₋₄alkylamino,diC₁₋₄alkylamino, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, aminocarbonyl,C₁₋₄alkylaminocarbonyl, diC₁₋₄alkylaminocarbonyl,C₁₋₄alkoxycarbonylamino, C₃₋₈cycloalkylC₀₋₆alkyl, phenylC₀₋₆alkyl,heteroarylC₀₋₆alkyl wherein the heteroaryl moiety is a 5- or 6-memberedaromatic ring which comprises 1, 2, 3 or 4 heteroatoms individuallyselected from N, O and S, heterocyclylC₀₋₆alkyl wherein the heterocyclylmoiety is a 5- or 6-membered non-aromatic ring which comprises 1, 2 or 3heteroatoms individually selected from N, O and S, and wherein any ofsaid cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties areoptionally substituted by 1, 2, 3, 4 or 5 substituents, which may be thesame or different, selected from R⁶; and

R⁶ represents methyl, methoxy or halogen;

or a salt or an N-oxide thereof.

The following list provides definitions, including preferreddefinitions, for substituents R¹, R², R³, R⁴, R⁵ and R⁶ with referenceto compounds of formula (I) for use in the method of controlling orpreventing infestation of a useful plant by phytopathogenicmicroorganisms. For any one of these substituents, any of thedefinitions given below may be combined with any definition of any othersubstituent given below or elsewhere in this document.

Preferably, R¹ and R² independently represent hydrogen or halogen. Morepreferably, R¹ and R² independently represent hydrogen, fluorine orchlorine. Most preferably, R¹ and R² are hydrogen or R¹ is hydrogen andR² is fluorine.

Preferably, R³ represents hydrogen or methyl. Most preferably, R³represents hydrogen.

Preferably, R⁴ represents (i) heterocyclylC₀₋₆alkyl wherein theheterocyclyl moiety is a 5- or 6-membered non-aromatic ring whichcomprises 1, 2 or 3 heteroatoms individually selected from N, O and S;(ii) C₃₋₈cycloalkylC₀₋₆alkyl; (iii) C₁₋₆alkyl wherein C₁₋₆alkyl isoptionally substituted by 1, 2 or 3 substituents, which may be the sameor different, selected from R⁵, which is C₁₋₄alkoxy, C₁₋₄alkylcarbonyl,C₁₋₄alkoxycarbonyl, hydroxyl, amino, C₁₋₄alkylamino, diC₁₋₄alkylamino,aminocarbonyl, C₁₋₄alkylaminocarbonyl, diC₁₋₄alkylaminocarbonyl; (iv)C₂₋₆alkenyl; (v) C₂₋₆alkynyl; (vi) phenylC₀₋₆alkyl; or (vii)heteroarylC₀₋₆alkyl wherein the heteroaryl moiety is a 5- or 6-memberedaromatic ring which comprises 1, 2, 3 or 4 heteroatoms individuallyselected from N, O and S, and wherein any of said cycloalkyl, phenyl,heteroaryl and heterocyclyl moieties are optionally substituted by 1, 2,3, 4 or 5 substituents, which may be the same or different, selectedfrom R⁵. More preferably, said heterocyclyl, cycloalkyl, phenyl orheteroaryl moieties are optionally substituted by 1 or 2 substituents,which may be the same or different, selected from R⁵.

Even more preferably, R⁴ represents (i) pyrrolidinyl, piperidinyl,(pyrrolidinyl)methyl, (piperidinyl)methyl, tetrahydrofuranyl,tetrahydropyranyl, 1,4-dioxanyl, (tetrahydrofuranyl)methyl,(tetrahydropyranyl)methyl, (1,4-dioxanyl)methyl, 1,3-dioxolanyl,(1,3-dioxolanyl)methyl, tetrahydrothienyl, tetrahydropyranyl,(tetrahydrothienyl)methyl or (tetrahydropyranyl)methyl, which isoptionally substituted by 1 or 2 substitutents, which may be the same ordifferent, selected from R⁵; (ii) cyclopropyl, (cyclopropyl)methyl,1-(cyclopropyl)ethyl, cyclobutyl, (cyclobutyl)methyl, cyclopentyl,(cyclopentyl)methyl, cyclohexyl, 1-(cyclohexyl)ethyl or cyclooctyl,optionally substituted by 1 or 2 substitutents, which may be the same ordifferent, selected from R⁵; (iii) C₁₋₆alkyl optionally substituted by 1or 2 substituents which may be the same or different, selected from R⁵,which is C₁₋₄alkoxy, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, hydroxyl,amino, C₁₋₄alkylamino, diC₁₋₄alkylamino, aminocarbonyl,C₁₋₄alkylaminocarbonyl, diC₁₋₄alkylaminocarbonyl; (iv) C₂₋₆alkenyl; (v)C₂₋₆alkynyl; (vi) phenylC₀₋₆alkyl optionally substituted by 1 or 2substituents, which may be the same or different, selected from R⁵; or(vii) heteroarylC₀₋₂alkyl, wherein the heteroaryl moiety of R⁴ is a5-membered ring comprising 1 or 2 heteroatoms individually selected fromN, O and S, and wherein the heteroarylC₀₋₂alkyl moiety is optionallysubstituted by 1 or 2 substituents, which may be the same or different,selected from R⁵.

Most preferably, R⁴ represents pyrrolidinyl, piperidinyl,(pyrrolidinyl)methyl, (piperidinyl)methyl, tetrahydrofuranyl,tetrahydropyranyl, 1,4-dioxanyl, (tetrahydrofuranyl)methyl,(tetrahydropyranyl)methyl, (1,4-dioxanyl)methyl, 1,3-dioxolanyl,(1,3-dioxolanyl)methyl, tetrahydrothienyl, tetrahydropyranyl,(tetrahydrothienyl)methyl or (tetrahydropyranyl)methyl, which isoptionally substituted by 1 or 2 substitutents, which may be the same ordifferent, selected from R⁵ wherein R⁵ represents methyl, ethyl,methoxy, methoxycarbonyl, ethoxycarbonyl, tert-butyloyxcarbonyl orbenzyl; or

cyclopropyl, (cyclopropyl)methyl, 1-(cyclopropyl)ethyl, cyclobutyl,(cyclobutyl)methyl, cyclopentyl, (cyclopentyl)methyl, cyclohexyl,1-(cyclohexyl)ethyl or cyclooctyl, optionally substituted by 1 or 2substitutents, which may be the same or different, selected from R⁵wherein R⁵ represents cyano, fluoro, methyl, cyclopropyl, phenyl orbenzyl; or

C₁₋₆alkyl optionally substituted by 1 or 2 substituents which may be thesame or different, selected from R⁵ wherein R⁵ represents C₁₋₄alkoxy orhydroxyl; or

C₂₋₆alkenyl, C₂₋₆alkynyl; or

phenylC₀₋₆alkyl optionally substituted by 1 or 2 substituents, which maybe the same or different, selected from R⁵ wherein R⁵ represents fluoro,chloro, methyl, methoxy, ethoxy or trifluoromethyl; or

heteroarylC₀₋₂alkyl, wherein the heteroaryl moiety of R⁴ is a 5-memberedring comprising 1 or 2 heteroatoms individually selected from N, O andS, and wherein the heteroarylC₀₋₂alkyl moiety is optionally substitutedby 1 or 2 substituents, which may be the same or different, selectedfrom R⁵ wherein R⁵ represents cyano, amino, chloro, bromo, methyl,t-butyl, methoxy or trifluoromethyl.

Preferably, R⁵ represents cyano, amino, halogen, hydroxyl, C₁₋₄alkyl,C₂₋₄alkynyl, haloC₁₋₄alkyl, C₁₋₄alkoxy, C₁₋₆alkylcarbonyl,C₁₋₄alkoxycarbonyl, C₁₋₄alkylaminocarbonyl, C₃₋₆cycloalkylC₀₋₂alkyl,phenylC₀₋₂alkyl, heterocyclylC₀₋₆alkyl, wherein the heterocyclyl moietyis a 5- or 6-membered non-aromatic ring which comprises 1, 2 or 3heteroatoms individually selected from N, O and S, and wherein any ofsaid cycloalkyl, phenyl and heterocyclyl moieties are optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R⁶.

Preferably, R¹ and R² independently represent hydrogen or halogen;

-   -   R³ represents hydrogen or methyl;    -   R⁴ represents pyrrolidinyl, piperidinyl, (pyrrolidinyl)methyl,        (piperidinyl)methyl, tetrahydrofuranyl, tetrahydropyranyl,        1,4-dioxanyl, (tetrahydrofuranyl)methyl,        (tetrahydropyranyl)methyl, (1,4-dioxanyl)methyl, 1,3-dioxolanyl,        (1,3-dioxolanyl)methyl, tetrahydrothienyl, tetrahydropyranyl,        (tetrahydrothienyl)methyl or (tetrahydropyranyl)methyl, which is        optionally substituted by 1 or 2 substitutents, which may be the        same or different, selected from R⁵; cyclopropyl,        (cyclopropyl)methyl, 1-(cyclopropyl)ethyl, cyclobutyl,        (cyclobutyl)methyl, cyclopentyl, (cyclopentyl)methyl,        cyclohexyl, 1-(cyclohexyl)ethyl or cyclooctyl, optionally        substituted by 1 or 2 substitutents, which may be the same or        different, selected from R⁵; C₁₋₆alkyl optionally substituted by        1 or 2 substituents which may be the same or different, selected        from R⁵, which is C₁₋₄alkoxy, C₁₋₄alkylcarbonyl,        C₁₋₄alkoxycarbonyl, hydroxyl, amino, C₁₋₄alkylamino,        diC₁₋₄alkylamino, aminocarbonyl, C₁₋₄alkylaminocarbonyl,        diC₁₋₄alkylaminocarbonyl; phenylC₀₋₆alkyl optionally substituted        by 1 or 2 substituents, which may be the same or different,        selected from R⁵; or heteroarylC₀₋₂alkyl, wherein the heteroaryl        moiety of R⁴ is a 5-membered ring comprising 1 or 2 heteroatoms        individually selected from N, O and S, and wherein the        heteroarylC₀₋₂alkyl moiety is optionally substituted by 1 or 2        substituents, which may be the same or different, selected from        R⁵;    -   R⁵ represents cyano, amino, halogen, hydroxyl, C₁₋₄alkyl,        C₂₋₄alkenyl, C₂₋₄alkynyl, haloC₁₋₄alkyl, C₁₋₄alkoxy,        C₁₋₆alkylcarbonyl, C₁₋₄alkoxycarbonyl, C₁₋₄alkylaminocarbonyl,        C₃₋₆cycloalkylC₀₋₂alkyl, phenylC₀₋₂alkyl, heterocyclylC₀₋₆alkyl,        wherein the heterocyclyl moiety is a 5- or 6-membered        non-aromatic ring which comprises 1, 2 or 3 heteroatoms        individually selected from N, O and S, and wherein any of said        cycloalkyl, phenyl and heterocyclyl moieties are optionally        substituted by 1, 2 or 3 substituents, which may be the same or        different, selected from R⁶; and    -   R⁶ represents methyl, methoxy or halogen.

More preferably, R¹ and R² independently represent hydrogen or halogen;

-   -   R³ represents hydrogen or methyl;    -   R⁴ represents pyrrolidinyl, piperidinyl, (pyrrolidinyl)methyl,        (piperidinyl)methyl, tetrahydrofuranyl, tetrahydropyranyl,        1,4-dioxanyl, (tetrahydrofuranyl)methyl,        (tetrahydropyranyl)methyl, (1,4-dioxanyl)methyl, 1,3-dioxolanyl,        (1,3-dioxolanyl)methyl, tetrahydrothienyl, tetrahydropyranyl,        (tetrahydrothienyl)methyl or (tetrahydropyranyl)methyl, which is        optionally substituted by 1 or 2 substitutents, which may be the        same or different, selected from R⁵ wherein R⁵ represents        methyl, ethyl, methoxy, methoxycarbonyl, ethoxycarbonyl,        tert-butyloyxcarbonyl or benzyl; or cyclopropyl,        (cyclopropyl)methyl, 1-(cyclopropyl)ethyl, cyclobutyl,        (cyclobutyl)methyl, cyclopentyl, (cyclopentyl)methyl,        cyclohexyl, 1-(cyclohexyl)ethyl or cyclooctyl, optionally        substituted by 1 or 2 substitutents, which may be the same or        different, selected from R⁵ wherein R⁵ represents cyano, fluoro,        methyl, cyclopropyl, phenyl or benzyl; or    -   C₁₋₆alkyl optionally substituted by 1 or 2 substituents which        may be the same or different, selected from R⁵ wherein R⁵        represents C₁₋₄alkoxy or hydroxyl; or    -   phenylC₀₋₆alkyl optionally substituted by 1 or 2 substituents,        which may be the same or different, selected from R⁵ wherein R⁵        represents fluoro, chloro, methyl, methoxy, ethoxy or        trifluoromethyl; or    -   heteroarylC₀₋₂alkyl, wherein the heteroaryl moiety of R⁴ is a        5-membered ring comprising 1 or 2 heteroatoms individually        selected from N, O and S, and wherein the heteroarylC₀₋₂alkyl        moiety is optionally substituted by 1 or 2 substituents, which        may be the same or different, selected from R⁵ wherein R⁵        represents cyano, amino, chloro, bromo, methyl, t-butyl, methoxy        or trifluoromethyl.

Also, in accordance with this disclosure, there is provided a compoundof formula (IA):

wherein

R¹ and R² independently represent hydrogen, halogen, methyl or methoxy;

R³ represents hydrogen or C₁₋₄alkyl;

R⁴ represents heterocyclylC₀₋₆alkyl wherein the heterocyclyl moiety is a5- or 6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, optionally substituted by 1, 2 or3 substitutents, which may be the same or different, selected from R⁵;

R⁵ represents C₁₋₄alkyl, C₁₋₄alkoxy, C₁₋₄alkoxycarbonyl,phenylC₀₋₂alkyl;

or a salt or an N-oxide thereof;

wherein the compound of formula (IA) is not a compound wherein R¹ ishydrogen and R², R³ and R⁴ are as follows:

R² R³ R⁴ R² R³ R⁴ H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

F H

H H

F H

H H

F H

H H

F H

H H

F H

H H

H —CH₂CH₂CH₃

H H

H H

Also, in accordance with this disclosure, there is provided a compoundof formula (IB):

wherein

R¹ and R² independently represent hydrogen, halogen, methyl or methoxy;

R³ represents hydrogen or C₁₋₄alkyl;

R⁴ represents C₃₋₈cycloalkylC₀₋₆alkyl optionally substituted by 1, 2, 3or 4 substitutents, which may be the same or different, selected fromR⁵;

R⁵ represents cyano, halogen, C₁₋₄alkyl, C₂₋₄alkynyl,C₁₋₄alkoxycarbonyl, C₃₋₆cycloalkylC₀₋₂alkyl, phenylC₀₋₂alkyl, andwherein any of said cycloalkyl or phenyl moieties are optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R⁶; and

R⁶ represents methyl, methoxy or halogen;

or a salt or an N-oxide thereof, and

wherein the compound according to Formula (IB) is not a compound whereinR¹ and R² are both hydrogen and R³ and R⁴ are as follows:

R³ R⁴ R³ R⁴ H

H

H

—CH₃

H

—CH₂CH₃

H

— —

Also, in accordance with this disclosure, there is provided a compoundof formula (IC):

wherein

R¹ and R² independently represent hydrogen, halogen, methyl or methoxy;

R³ represents hydrogen or C₁₋₄alkyl;

R⁴ represents C₁₋₆alkyl, C₂₋₆alkenyl or C₂₋₆alkynyl, wherein C₁₋₆alkylis optionally substituted by 1, 2 or 3 substituents, which may be thesame or different, selected from R⁵;

R⁵ represents halogen, C₁₋₄alkoxy, C₁₋₄alkylcarbonyl,C₁₋₄alkoxycarbonyl, hydroxyl, C₁₋₄alkylaminocarbonyl;

or a salt or an N-oxide thereof, and

wherein the compound according to Formula (IC) is not a compound whereR¹ and R² are both hydrogen and R³ and R⁴ are as follows:

R³ R⁴ R³ R⁴ H —CH₃ H —CH₂CH₂CH₂CH₃ H —CH₂CH₃ H —CH(CH₂OH)(CH₂CH(CH₃)₂) H—CH₂CH₂OH H —C(CH₃)(CH₂CH₂CH₃)C(O)OCH₃ H —CH₂CH₂OCH₃ H C(CH₃)₂CH₂OCH₃ H—CH₂CH₂CH₂OH H —CH(CH(CH₃)₂)C(O)OCH₃ H —C(H)(CH₃)₂ H —CH₂C(O)NH(C(CH₃)₃)H —CH₂CH₂CH₂OCH₃ H —CH(CH₃)C(O)OCH₃ H —CH₂CH₂F —CH₃ —CH₃ H—CH₂C(H)(CH₃)₂ —CH₃ —CH₂CH₃ H —CH(CH₃)CH₂OH —CH₃ —CH₂CH₂OH H—CH(CH₂CH₃)₂ —CH₃ —CH₂CH₂OCH₃ H —CH(CH₂CH₃)(CH₂OH) —CH₃ —CH(CH₃)₂ H—CH₂C(O)NHCH₃ — —;

or is not a compound according to Formula (IC) wherein R¹ is hydrogen,R² is fluorine, R³ is hydrogen, and R⁴ is —CH(CH₃)CH₂OH.

Also, in accordance with this disclosure, there is provided a compoundof formula (ID):

wherein

R¹ and R² independently represent hydrogen, halogen, methyl or methoxy;

R³ represents hydrogen or C₁₋₄alkyl;

R⁴ represents a phenylC₀₋₆alkyl optionally substituted by 1, 2, 3, 4 or5 substitutents, which may be the same or different, selected from R⁵;

R⁵ represents cyano, halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl,C₂₋₄alkynyl, haloC₁₋₄alkyl, C₁₋₄alkoxy, C₁₋₄alkylcarbonyl,C₁₋₄alkoxycarbonyl, aminocarbonyl, C₁₋₄alkylaminocarbonyl,diC₁₋₄alkylaminocarbonyl, C₁₋₄alkoxycarbonylamino,C₃₋₈cycloalkylC₀₋₆alkyl, phenylC₀₋₆alkyl, heteroarylC₀₋₆alkyl whereinthe heteroaryl moiety is a 5- or 6-membered aromatic ring whichcomprises 1, 2, 3 or 4 heteroatoms individually selected from N, O andS, heterocyclylC₀₋₆alkyl wherein the heterocyclyl moiety is a 5- or6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, and wherein any of saidcycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionallysubstituted by 1, 2, 3, 4 or 5 substituents, which may be the same ordifferent, selected from R⁶; and

R⁶ represents methyl, methoxy or halogen;

or a salt or an N-oxide thereof, and

wherein the compound according to Formula (I) is not a compound wheretogether R¹ and R² are hydrogen and R³ and R⁴ are as follows:

R³ R⁴ R³ R⁴ H —Ph H -(2-Cl-5-OCH₃)Ph H —CH₂(4-(N- H -(3-Cl-6-OCH₃)Phmorpholinyl)methyl)Ph H —CH₂CH₂Ph H -(2-CH₃-4-Cl)Ph H —CH₂Ph H -(2-Cl)PhH —CH(CH₃)(4-CN)Ph H -(4-CH₃)Ph H —CH₂(3-CH₂OCH₃)Ph H -(2-OCH₃-5-OCH₃)PhH —CH₂(3-F-4-(N- H -(2-Cl-5-F)Ph piperazinyl)Ph H -(3-CN)Ph H-(2-Cl-4-F)Ph H -(3-Cl-4-OCH₃)Ph H -(2-Cl-4-OCH₃)Ph H —CH₂CH(OH)(3-F)PhH -(2-OCH₃-5-CH₃)Ph H -(2-OH)Ph H -(2-OH-5-CN)Ph H -(3-OCH₃-4-OCH₃)Ph H-(2-C(O)NH(CH₃))Ph H -(2-OH-3-Cl)Ph H -(2-Cl-5-CN)Ph H-(3-OCH₃-5-OCH₃)Ph H -(2-CN-3-F)Ph H -(2-OCH₃-4-OCH₃)Ph —CH₃ —CH₂(2-F)PhH -(3-F-4-CH₃)Ph —CH₃ —CH₂Ph H -(3-OCH₃)Ph —CH₃ —Ph H -(2-CH₃)Ph —CH₂CH₃—CH₂CH₂Ph H -(2-OH-5-Cl)Ph — —

Also, in accordance with this disclosure, there is provided a compoundof formula (IE):

wherein

R¹ and R² independently represent hydrogen, halogen, methyl or methoxy;

R³ represents hydrogen or C₁₋₄alkyl;

R⁴ represents heteroarylC₀₋₆alkyl wherein the heteroaryl moiety is a 5-or 6-membered ring comprising 1, 2, 3 or 4 heteroatoms individuallyselected from N, O and S, and wherein the heteroarylC₀₋₆alkyl moiety isoptionally substituted by 1, 2, 3, 4 or 5 substitutents, which may bethe same or different, selected from R⁵;

R⁵ represents cyano, amino, halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl,C₂₋₄alkynyl, haloC₁₋₄alkyl, C₁₋₄alkoxy, C₁₋₄alkylamino,diC₁₋₄alkylamino, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, aminocarbonyl,C₁₋₄alkylaminocarbonyl, diC₁₋₄alkylaminocarbonyl,C₁₋₄alkoxycarbonylamino, C₃₋₈cycloalkylC₀₋₆alkyl, phenylC₀₋₆alkyl,heteroarylC₀₋₆alkyl wherein the heteroaryl moiety is a 5- or 6-memberedaromatic ring which comprises 1, 2, 3 or 4 heteroatoms individuallyselected from N, O and S, heterocyclylC₀₋₆alkyl wherein the heterocyclylmoiety is a 5- or 6-membered non-aromatic ring which comprises 1, 2 or 3heteroatoms individually selected from N, O and S, and wherein any ofsaid cycloalkyl, phenyl, heteroaryl and heterocyclyl are optionallysubstituted by 1, 2, 3, 4 or 5 substitutents, which may be the same ordifferent, selected from R⁶; and

R⁶ represents methyl, methoxy or halogen;

or a salt or a N-oxide thereof;

wherein the compound of formula (I) is not a compound wherein R¹ ishydrogen and R², R³ and R⁴ are as follows.

R² R³ R⁴ R² R³ R⁴ H H

H H

H H

H H

H H

H CH₃

H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

F H

H H

H CH₃

H H

H H

H H

H H

H H

H H

H H

H H

— — —

Further according to this disclosure, there may be provided a compoundof formula (ID):

wherein

R¹ and R² independently represent hydrogen, halogen, methyl or methoxy;

R³ represents hydrogen or C₁₋₄alkyl;

R⁴ represents a phenylC₀₋₆alkyl optionally substituted by 1 or 2substitutents, which may be the same or different, selected from R⁵;

R⁵ represents halogen, C₁₋₄alkyl, haloC₁₋₄alkyl, C₁₋₄alkoxy orheterocyclylC₀₋₆alkyl, wherein the heterocyclyl moiety is a 5- or6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, and wherein said heterocyclylmoiety is optionally substituted by 1 or 2 substituents, which may bethe same or different, selected from R⁶; and

R⁶ represents methyl, methoxy or halogen;

or a salt or an N-oxide thereof, and

wherein the compound according to Formula (ID) is not a compound whereinR¹ and R² are both hydrogen and R³ and R⁴ are as follows:

R³ R⁴ R³ R⁴ H —Ph H -(3-Cl-6-OCH₃)Ph H —CH₂(4-(N- H -(2-CH₃-4-Cl)Phmorpholinyl)methyl)Ph H —CH₂CH₂Ph H -(2-Cl)Ph H —CH₂Ph H -(4-CH₃)Ph H—CH₂(3-CH₂OCH₃)Ph H -(2-OCH₃-5-OCH₃)Ph H —CH₂(3-F-4-(N- H -(2-Cl-5-F)Phpiperazinyl)Ph H -(3-Cl-4-OCH₃)Ph H -(2-Cl-4-F)Ph H -(3-OCH₃-4-OCH₃)Ph H-(2-Cl-4-OCH₃)Ph H -(3-OCH₃-5-OCH₃)Ph H -(2-OCH₃-5-CH₃)Ph H-(2-OCH₃-4-OCH₃)Ph —CH₃ —CH₂(2-F)Ph H -(3-F-4-CH₃)Ph —CH₃ —CH₂Ph H-(3-OCH₃)Ph —CH₃ —Ph H -(2-CH₃)Ph —CH₂CH₃ —CH₂CH₂Ph H -(2-Cl-5-OCH₃)Ph ——

Further according to this disclosure, there may be provided a compoundof formula (IE):

wherein

R¹ and R² independently represent hydrogen, halogen, methyl or methoxy;

R³ represents hydrogen or C₁₋₄alkyl;

R⁴ represents heteroarylC₀₋₆alkyl wherein the heteroaryl moiety is a 5-or 6-membered ring comprising 1, 2, 3 or 4 heteroatoms individuallyselected from N, O and S, and wherein the heteroarylC₀₋₆alkyl moiety isoptionally substituted by 1, 2 or 3 substitutents, which may be the sameor different, selected from R⁵;

R⁵ represents cyano, amino, halogen, C₁₋₄alkyl, haloC₁₋₂alkyl orC₁₋₂alkoxy; or a salt or a N-oxide thereof;

wherein the compound of formula (IE) is not a compound wherein R¹ ishydrogen and R², R³ and R⁴ are as follows:

R² R³ R⁴ R² R³ R⁴ H H

H H

H H

H H

H H

H H

H H

H CH₃

H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

H H

F H

H H

H CH₃

H H

H H

H H

H H

H H

In accordance with this disclosure as far as it relates to a compound ofFormula (IA), (IB), (IC), (ID) or (IE), the following list providesdefinitions, including preferred definitions, for substituents R¹, R²,R³, R⁴, R⁵ and R⁶. For any one of these substituents, any of thedefinitions given below may be combined with any definition of any othersubstituent given below or elsewhere in this document.

In accordance with a compound of Formula (IA), preferably, R¹ and R²independently represent hydrogen, fluoro, chloro, methyl or methoxy.More preferably, R¹ is hydrogen and R² is halogen (preferably fluorine),methyl or methoxy. In a preferred embodiment, R² is a halogen, inparticular, fluorine.

Preferably, R³ represents hydrogen or methyl, and more preferablyhydrogen.

Preferably, R⁴ represents heterocyclylC₀₋₂alkyl wherein the heterocyclylmoiety is a 5- or 6-membered non-aromatic ring which comprises 1, 2 or 3heteroatoms individually selected from N, O and S, and wherein theheterocyclylC₀₋₂alkyl moiety is optionally substituted by 1 or 2substitutents, which may be the same or different, selected from R⁵.More preferably, R⁴ represents heterocyclylC₀₋₁alkyl wherein theheterocyclyl moiety is a 5- or 6-membered non-aromatic ring whichcomprises 1 or 2 heteroatoms individually selected from N, O and S, andwherein the heterocyclylC₀₋₁alkyl moiety is optionally substituted by 1or 2 substitutents, which may be the same or different, selected fromR⁵. Even more preferably, R⁴ represents heterocyclylC₀₋₁alkyl whereinthe heterocyclyl moiety is a 5- or 6-membered non-aromatic ring whichcomprises 1 or 2 heteroatoms individually selected from N and O, andwherein the heterocyclylC₀₋₁alkyl moiety is optionally substituted by 1substitutent, which may be the same or different, selected from R⁵.

In certain embodiments, R⁴ may be a pyrrolidinyl, piperidinyl,(pyrrolidinyl)methyl, (piperidinyl)methyl, tetrahydrofuranyl,tetrahydropyranyl, 1,4-dioxanyl, (tetrahydrofuranyl)methyl,(tetrahydropyranyl)methyl, (1,4-dioxanyl)methyl, 1,3-dioxolanyl,(1,3-dioxolanyl)methyl, tetrahydrothienyl, tetrahydropyranyl,(tetrahydrothienyl)methyl or (tetrahydropyranyl)methyl, which isoptionally substituted by 1 or 2 substitutents, which may be the same ordifferent, selected from R⁵.

Preferably, R⁵ represents methyl, methoxy, methoxycarbonyl,tert-butyloyxcarbonyl or benzyl.

Preferably, R¹ and R² independently represent hydrogen, halogen, methylor methoxy;

R³ represents hydrogen or C₁₋₄alkyl; and

R⁴ represents heterocyclylC₀₋₂alkyl wherein the heterocyclyl moiety is a5- or 6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, and wherein theheterocyclylC₀₋₂alkyl moiety is optionally substituted by 1 or 2substitutents, which may be the same or different, selected from R⁵,wherein R⁵ is selected from C₁₋₄alkyl, C₁₋₄alkoxy, C₁₋₄alkoxycarbonyl.

More preferably, R¹ and R² independently represent hydrogen, fluoro,chloro, methyl or methoxy;

R³ represents hydrogen, methyl, ethyl or n-propyl; and

R⁴ represents heterocyclylC₀₋₁alkyl wherein the heterocyclyl moiety is a5- or 6-membered non-aromatic ring which comprises 1 or 2 heteroatomsindividually selected from N and O, and wherein theheterocyclylC₀₋₁alkyl moiety is optionally substituted by 1 or 2substitutents, which may be the same or different, selected from R⁵,wherein R⁵ is selected from C₁₋₄alkyl, C₁₋₄alkoxy, C₁₋₄alkoxycarbonyl.

Even more preferably, R¹ and R² independently represent hydrogen orfluoro;

R³ represents hydrogen, methyl, ethyl or n-propyl; and

R⁴ represents a heterocyclylC₀₋₁alkyl wherein the heterocyclyl moiety isa 5- or 6-membered non-aromatic ring which comprises 1 or 2 heteroatomsindividually selected from N and O, and wherein theheterocyclylC₀₋₁alkyl moiety is optionally substituted by 1 or 2substitutents, which may be the same or different, selected from R⁵,wherein R⁵ is selected from methyl, methoxy, methoxycarbonyl ortert-butyloxycarbonyl.

Most preferably, R¹ represents hydrogen and R² represents hydrogen orfluoro;

R³ represents hydrogen, methyl, ethyl or n-propyl; and

R⁴ represents pyrrolidinyl, piperidinyl, (pyrrolidinyl)methyl,(piperidinyl)methyl, tetrahydrofuranyl, (tetrahydrofuranyl)methyl,(tetrahydropyranyl)methyl, (1,4-dioxanyl)methyl, (1,3-dioxolanyl)methyl,tetrahydrothienyl or tetrahydrothiopyranyl optionally substituted by 1or 2 substituents which may be the same or different, selected from R⁵,wherein R⁵ is selected from methyl, methoxy, methoxycarbonyl ortert-butyloxycarbonyl.

In accordance with a compound of Formula (IB), preferably, R¹ and R²independently represent hydrogen, fluoro, chloro, methyl or methoxy.More preferably, R¹ is hydrogen and R² is halogen (preferably fluorine),methyl or methoxy. In a preferred embodiment, R² is a halogen, inparticular, fluorine.

Preferably, R³ represents hydrogen, methyl or ethyl, and more preferablyhydrogen.

Preferably, R⁴ is cyclopropyl, (cyclopropyl)methyl,1-(cyclopropyl)ethyl, cyclobutyl, (cyclobutyl)methyl, cyclopentyl,(cyclopentyl)methyl, cyclohexyl, 1-(cyclohexyl)ethyl or cyclooctyl,optionally substituted by 1 or 2 substitutents, which may be the same ordifferent, selected from R⁵.

Preferably, R⁵ represents cyano, fluoro, methyl, ethynyl, cyclopropyl,phenyl or benzyl, wherein cyclopropyl and phenyl moieties are optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R⁶.

Preferably, R⁶ represents chloro.

Preferably, R¹ and R² independently represent hydrogen, halogen, methylor methoxy;

R³ represents hydrogen or C₁₋₄alkyl; and

R⁴ represents C₃₋₆cycloalkylC₀₋₂alkyl optionally substituted by 1 or 2substitutents, which may be the same or different, selected from R⁵,wherein R⁵ represents cyano, fluoro, methyl, ethynyl, cyclopropyl,phenyl or benzyl wherein cyclopropyl and phenyl moieties are optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R⁶, wherein R⁶ represents chloro.

More preferably, R¹ and R² independently represent hydrogen, fluoro,chloro, methyl or methoxy;

R³ represents hydrogen, methyl or ethyl or n-propyl; and

R⁴ represents cyclopropyl, (cyclopropyl)methyl, 1-(cyclopropyl)ethyl,cyclobutyl, (cyclobutyl)methyl, cyclopentyl, (cyclopentyl)methyl,cyclohexyl, 1-(cyclohexyl)ethyl or cyclooctyl, optionally substituted by1 or 2 substitutents, which may be the same or different, selected fromR⁵, R⁵ represents cyano, fluoro, methyl, ethynyl, cyclopropyl, phenyl orbenzyl wherein cyclopropyl and phenyl moieties are optionallysubstituted by 1 substituent selected from R⁶, wherein R⁶ representschloro.

Even more preferably, R¹ and R² independently represent hydrogen orfluoro;

R³ represents hydrogen, methyl, ethyl or n-propyl; and

R⁴ represents C₃₋₆cycloalkylC₀₋₂alkyl optionally substituted by 1 or 2substitutents, which may be the same or different, selected from R⁵,wherein R⁵ represents cyano, fluoro, methyl, ethynyl, cyclopropyl,phenyl or benzyl wherein cyclopropyl and phenyl moieties are optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R⁶, wherein R⁶ represents chloro.

Most preferably, R¹ is hydrogen and R² is halogen (preferably fluorine),

R³ represents hydrogen; and

R⁴ represents cyclopropyl, (cyclopropyl)methyl, 1-(cyclopropyl)ethyl,cyclobutyl, (cyclobutyl)methyl, cyclopentyl, (cyclopentyl)methyl,cyclohexyl, 1-(cyclohexyl)ethyl or cyclooctyl, optionally substituted by1 or 2 substitutents, which may be the same or different, selected fromR⁵, R⁵ represents cyano, fluoro, methyl, ethynyl, cyclopropyl, phenyl orbenzyl wherein cyclopropyl and phenyl moieties are optionallysubstituted by 1 substituent selected from R⁶, wherein R⁶ representschloro.

In accordance with a compound of Formula (IC), preferably, R¹ and R²independently represent hydrogen, fluoro, chloro, methyl or methoxy.More preferably, R¹ is hydrogen and R² is hydrogen, halogen (preferablyfluorine), methyl or methoxy. In a preferred embodiment, R¹ is hydrogenand R² is a halogen, in particular, fluorine, or R¹ and R² are hydrogen.

Preferably, R³ represents hydrogen, methyl, ethyl, iso-propyl, and morepreferably hydrogen.

Preferably, R⁴ represents C₁₋₆alkyl, C₂₋₆alkenyl or C₂₋₆alkynyl, whereinC₁₋₆alkyl is optionally substituted by 1 or 2 substituents which may bethe same or different, selected from R⁵, wherein R⁵ representsC₁₋₄alkoxy or hydroxyl. More preferably, R⁴ represents C₁₋₆alkyl,C₂₋₆alkenyl or C₂₋₆alkynyl, wherein C₁₋₆alkyl is optionally substitutedby 1 substituent selected from R⁵, wherein R⁵ represents C₁₋₄alkoxy orhydroxyl. Even more preferably, R⁴ represents C₁₋₆alkyl optionallysubstituted by 1 substituent selected from R⁵, wherein R⁵ representshydroxyl; or R⁴ represents C₂₋₆alkenyl or C₂₋₆alkynyl.

Preferably, R¹ and R² independently represent hydrogen, halogen, methylor methoxy;

R³ represents hydrogen or C₁₋₄alkyl; and

R⁴ represents C₂₋₆alkenyl, C₂₋₆alkynyl or C₁₋₆alkyl optionallysubstituted by 1 or 2 substituents which may be the same or different,selected from R⁵, wherein R⁵ represents C₁₋₄alkoxy or hydroxyl.

More preferably, R¹ is hydrogen and R² is halogen;

R³ represents hydrogen, methyl or ethyl;

R⁴ represents C₂₋₆alkenyl, C₂₋₆alkynyl or C₁₋₆alkyl optionallysubstituted by 1 or 2 substituents which may be the same or different,selected from R⁵, wherein R⁵ represents C₁₋₄alkoxy or hydroxyl.

Even more preferably, R¹ and R² are hydrogen, or R¹ is hydrogen and R²is fluorine;

R³ represents hydrogen or methyl;

R⁴ represents C₂₋₆alkenyl, C₂₋₆alkynyl or C₁₋₆alkyl optionallysubstituted by 1 substituent selected from R⁵, wherein R⁵ representsC₁₋₄alkoxy or hydroxyl.

Most preferably, R¹ and R² are hydrogen, or R¹ is hydrogen and R² isfluorine;

R³ represents hydrogen;

R⁴ represents C₂₋₆alkenyl, C₂₋₆alkynyl or C₁₋₆alkyl optionallysubstituted by 1 substituent selected from R⁵, wherein R⁵ representsC₁₋₄alkoxy or hydroxyl.

In accordance with a compound of Formula (ID), preferably, R¹ and R²independently represent hydrogen, fluoro, chloro, methyl or methoxy.More preferably, R¹ and R² independently represent hydrogen and fluoro.Even more preferably, R¹ is hydrogen and R² is halogen (preferablyfluorine), methyl or methoxy. In a preferred embodiment, R² is ahalogen, in particular fluorine.

Preferably, R³ represents hydrogen or methyl.

Preferably, R⁴ represents a phenylC₀₋₂alkyl optionally substituted by 1,2, 3, 4 or 5 substituents, which may be the same or different, selectedfrom R⁵. More preferably, R⁴ represents a phenylC₀₋₁alkyl optionallysubstituted by 1, 2, 3, 4 or 5 substituents, which may be the same ordifferent, selected from R⁵. Even more preferably, R⁴ represents aphenylC₀₋₆alkyl optionally substituted by 1 or 2 substituents, which maybe the same or different, selected from R⁵. Further more preferably, R⁴represents phenylC₀₋₂alkyl optionally substituted by 1 or 2substitutents, which may be the same or different, selected from R⁵,which is preferably selected from fluoro, chloro, methoxy, methyl,ethyl, trifluoromethyl or N-morpholinyl, wherein preferably the 1 or 2substitutents which may be the same or different, selected from R⁵, arephenyl ring substituents.

Preferably, R¹ and R² independently represent hydrogen, halogen, methylor methoxy;

-   -   R³ represents hydrogen or C₁₋₄alkyl;    -   R⁴ represents a phenylC₀₋₆alkyl optionally substituted by 1, 2,        3, 4 or 5 substituents, which may be the same or different,        selected from R⁵.

More preferably, R¹ and R² independently represent hydrogen, fluoro,chloro, methyl or methoxy;

-   -   R³ represents hydrogen or methyl;    -   R⁴ represents a phenylC₀₋₂alkyl optionally substituted by 1, 2,        3, 4 or 5 substituents, which may be the same or different,        selected from R⁵.

Even more preferably, R¹ and R² independently represent hydrogen andfluoro;

-   -   R³ represents hydrogen or methyl;    -   R⁴ represents a phenylC₀₋₁alkyl optionally substituted by 1, 2,        3, 4 or 5 substituents, which may be the same or different,        selected from R⁵.

Most preferably, R¹ and R² independently represent hydrogen and fluoro;

-   -   R³ represents hydrogen or methyl;    -   R⁴ represents a phenylC₀₋₁alkyl optionally substituted by 1, 2        or 3 substituents, which may be the same or different, selected        from R⁵.

Preferably, R⁵ represents cyano, halogen, hydroxy, C₁₋₄alkyl,C₂₋₃alkenyl, C₂₋₃alkynyl, haloC₁₋₂alkyl, C₁₋₂alkoxy, C₁₋₂alkylcarbonyl,C₁₋₂alkoxycarbonyl, aminocarbonyl, C₁₋₂alkylaminocarbonyl,diC₁₋₂alkylaminocarbonyl, C₁₋₂alkoxycarbonylamino,C₃₋₈cycloalkylC₀₋₂alkyl, phenylC₀₋₂alkyl, heteroarylC₀₋₂alkyl whereinthe heteroaryl moiety is a 5- or 6-membered aromatic ring whichcomprises 1, 2, 3 or 4 heteroatoms individually selected from N, O andS, heterocyclylC₀₋₂alkyl wherein the heterocyclyl moiety is a 5- or6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, and wherein any of saidcycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionallysubstituted by 1, 2, 3, 4 or 5 substituents, which may be the same ordifferent, selected from R⁶.

More preferably, R⁵ represents cyano, halogen, C₁₋₄alkyl, haloC₁₋₂alkyl,C₁₋₂alkoxy, C₁₋₂alkylcarbonyl, C₁₋₂alkoxycarbonyl, aminocarbonyl,C₁₋₂alkylaminocarbonyl, diC₁₋₂alkylaminocarbonyl,C₁₋₂alkoxycarbonylamino, C₃₋₈cycloalkylC₀₋₂alkyl, phenylC₀₋₂alkyl,heteroarylC₀₋₂alkyl wherein the heteroaryl moiety is a 5- or 6-memberedaromatic ring which comprises 1, 2, 3 or 4 heteroatoms individuallyselected from N, O and S, heterocyclylC₀₋₂alkyl wherein the heterocyclylmoiety is a 5- or 6-membered non-aromatic ring which comprises 1, 2 or 3heteroatoms individually selected from N, O and S, and wherein any ofsaid cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties areoptionally substituted by 1, 2 or 3 substituents, which may be the sameor different, selected from R⁶.

Even more preferably, R⁵ represents cyano, halogen, C₁₋₄alkyl,haloC₁₋₂alkyl, C₁₋₂alkoxy, C₁₋₂alkylcarbonyl, C₁₋₂alkoxycarbonyl,aminocarbonyl, C₁₋₂alkylaminocarbonyl, diC₁₋₂alkylaminocarbonyl,C₁₋₂alkoxycarbonylamino, C₃₋₈cycloalkylC₀₋₂alkyl wherein any of saidmoieties is optionally substituted by 1, 2, or 3 substituents, which maybe the same or different, selected from R⁶.

Most preferably, R⁵ represents cyano, halogen, C₁₋₄alkyl, haloC₁₋₂alkyl,C₁₋₂alkoxy, aminocarbonyl, wherein any of said moieties are optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R⁶.

Preferably, R⁶ represents methyl, methoxy, fluoro or chloro.

In certain embodiments of this disclosure, it is preferred that R⁵represents halogen, C₁₋₄alkyl, haloC₁₋₄alkyl, C₁₋₄alkoxy,C₃₋₈cycloalkylC₀₋₆alkyl, phenylC₀₋₆alkyl, heteroarylC₀₋₆alkyl whereinthe heteroaryl moiety is a 5- or 6-membered aromatic ring whichcomprises 1, 2, 3 or 4 heteroatoms individually selected from N, O andS, heterocyclylC₀₋₆alkyl wherein the heterocyclyl moiety is a 5- or6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, and wherein any of saidcycloalkyl, phenyl, heteroaryl and heterocyclyl moieties is optionallysubstituted by a substituent selected from R⁶, wherein R⁶ representsmethyl, methoxy or halogen.

More preferably in accordance with this embodiment, R⁵ representshalogen, C₁₋₄alkyl, haloC₁₋₄alkyl, C₁₋₄alkoxy or heterocyclylC₀₋₆alkylwherein the heterocyclyl moiety is a 5- or 6-membered non-aromatic ringwhich comprises 1, 2 or 3 heteroatoms individually selected from N, Oand S.

In accordance with a compound of Formula (IE), preferably, R¹ and R²independently represent hydrogen, fluoro, chloro, methyl or methoxy.More preferably, R¹ is hydrogen and R² is halogen (preferably fluorine),methyl or methoxy. In a preferred embodiment, R² is a halogen, inparticular, fluorine.

Preferably, R³ represents hydrogen or methyl, and more preferablyhydrogen.

Preferably, R⁴ represents heteroarylC₀₋₂alkyl wherein the heteroarylmoiety is a 5- or 6-membered ring comprising 1, 2 or 3 heteroatomsindividually selected from N, O and S, and wherein theheteroarylC₀₋₂alkyl moiety is optionally substituted by 1 or 2substituents, which may be the same or different, selected from R⁵. Insome embodiments, R⁴ is not a 4-pyridyl substituent.

In another embodiment, R⁴ represents heteroarylC₀₋₂alkyl, wherein theheteroaryl moiety of R⁴ is a 5-membered ring comprising 1 or 2heteroatoms individually selected from N, O and S, and wherein theheteroarylC₀₋₂alkyl moiety is optionally substituted by 1 or 2substituents, which may be the same or different, selected from R⁵.According to this embodiment, preferably, at least one heteroatom is S,and more preferably, R⁴ is a thienyl derivative, in particular, a2-thienyl derivative.

In other embodiments of the invention, R⁴ is unsubstituted.

Preferably, R⁵ represents amino, cyano, halogen, hydroxy, C₁₋₄alkyl,C₂₋₃alkenyl, C₂₋₃alkynyl, haloC₁₋₂alkyl, C₁₋₂alkoxy, C₁₋₂alkylcarbonyl,C₁₋₂alkoxycarbonyl, aminocarbonyl, C₁₋₂alkylaminocarbonyl,diC₁₋₂alkylaminocarbonyl, C₁₋₂alkoxycarbonylamino,C₃₋₈cycloalkylC₀₋₂alkyl, phenylC₀₋₂alkyl, heteroarylC₀₋₂alkyl whereinthe heteroaryl moiety is a 5- or 6-membered aromatic ring whichcomprises 1, 2, 3 or 4 heteroatoms individually selected from N, O andS, heterocyclylC₀₋₂alkyl wherein the heterocyclyl moiety is a 5- or6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, and wherein any of saidcycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionallysubstituted by 1, 2, 3, 4 or 5 substituents, which may be the same ordifferent, selected from R⁶.

More preferably, R⁵ represents amino, cyano, halogen, C₁₋₄alkyl,haloC₁₋₂alkyl, C₁₋₂alkoxy, C₁₋₂alkylcarbonyl, C₁₋₂alkoxycarbonyl,aminocarbonyl, C₁₋₂alkylaminocarbonyl, diC₁₋₂alkylaminocarbonyl,C₁₋₂alkoxycarbonylamino, C₃₋₈cycloalkylC₀₋₂alkyl wherein any of saidmoieties are optionally substituted by 1, 2, or 3 substituents, whichmay be the same or different, selected from R⁶.

Even more preferably, R⁵ represents amino, cyano, halogen, C₁₋₄alkyl,haloC₁₋₂alkyl, C₁₋₂alkoxy, aminocarbonyl, wherein any of said moietiesare optionally substituted by 1, 2 or 3 substituents, which may be thesame or different, selected from R⁶. Most preferably, R⁵ is selectedfrom amino, cyano, halogen, C₁₋₄alkyl, haloC₁₋₂alkyl or C₁₋₂alkoxy.

Preferably, R⁶ represents methyl, methoxy, fluoro or chloro.

Preferably, R¹ and R² independently represent hydrogen, halogen, methylor methoxy;

-   -   R³ represents hydrogen or C₁₋₄alkyl; and    -   R⁴ represents a R⁴ represents heteroarylC₀₋₂alkyl wherein the        heteroaryl moiety is a 5- or 6-membered ring comprising 1, 2 or        3 heteroatoms individually selected from N, O and S, and wherein        the heteroarylC₀₋₂alkyl moiety is optionally substituted by 1 or        2 substituents, which may be the same or different, selected        from R⁵, wherein R⁵ is selected from amino, cyano, halogen,        C₁₋₄alkyl, haloC₁₋₂alkyl or C₁₋₂alkoxy, and wherein R⁴ is not an        optionally substituted 4-pyridyl substituent.

More preferably, R¹ and R² independently represent hydrogen, fluoro,chloro, methyl or methoxy;

-   -   R³ represents hydrogen or methyl; and    -   R⁴ represents a represents heteroarylC₀₋₂alkyl, wherein the        heteroaryl moiety of R⁴ is a 5-membered ring comprising 1 or 2        heteroatoms individually selected from N, O and S, and wherein        heteroarylC₀₋₂alkyl is optionally substituted by 1 or 2        substitutents, which may be the same or different, selected from        R⁵, wherein R⁵ is selected from amino, cyano, halogen,        C₁₋₄alkyl, haloC₁₋₂alkyl or C₁₋₂alkoxy.

Even more preferably, R¹ and R² independently represent hydrogen orfluoro;

-   -   R³ represents hydrogen; and    -   R⁴ represents a heteroarylC₀₋₂alkyl wherein the heteroaryl        moiety is a 5- or 6-membered ring comprising 1, 2 or 3        heteroatoms individually selected from N, O and S, and wherein        the heteroarylC₀₋₂alkyl moiety is optionally substituted by 1 or        2 substituents, which may be the same or different, selected        from R⁵, wherein R⁵ is selected from amino, cyano, halogen,        C₁₋₄alkyl, haloC₁₋₂alkyl or C₁₋₂alkoxy.

Most preferably, R¹ and R² independently represent hydrogen and fluoro;

-   -   R³ represents hydrogen; and    -   R⁴ represents a heteroarylC₀₋₁alkyl wherein the heteroaryl        moiety is a 5- or 6-membered ring comprising 1, 2 or 3        heteroatoms individually selected from N, O and S, and wherein        the heteroarylC₀₋₁alkyl moiety is optionally substituted by 1 or        2 substituents, which may be the same or different, selected        from R⁵, wherein R⁵ is selected from amino, cyano, halogen,        C₁₋₄alkyl, haloC₁₋₂alkyl or C₁₋₂alkoxy.

In accordance with the definition of R⁴ for compounds of Formula (IE),preferred heteroaryl fragments in the definition of heteroarylC₀₋₆alkyl,heteroarylC₀₋₂alkyl, heteroarylC₀₋₁alkyl, etc, include thienyl,pyrazolyl, pyridyl, triazolyl, furanyl and thiazolyl moieties.

It is understood that when in aqueous media, the compounds of formula(I) according to the invention may be present in a reversibleequilibrium with the corresponding covalently hydrated forms (ie, thecompounds of formula (I-I) and formula (I-II) as shown below) at theCF₃-oxadiazole motif. This dynamic equilibrium may be important for thebiological activity of the compounds of Formula (I). The designations ofR¹, R², R³, R⁴ (including, R^(4A), R^(4B), R^(4C), R^(4D), R^(4E)), R⁵(including, R^(5A), R^(5B), R^(5C), R^(5D), R^(5E)) and R⁶ (including,R^(6B), R^(6D), R^(6E)), with reference to the compounds of formula (I)of the present invention apply generally to the compounds of Formula(I-I) and Formula (I-I), as do the specific disclosures of combinationsof R¹, R², R³, R⁴ (including, R^(4A), R^(4B), R^(4C), R^(4D), R^(4E)),R⁵ (including, R^(5A)R^(5B), R^(5C), R^(5D), R^(5E)) and R⁶ (including,R^(6B), R^(6D), R^(6E)) as represented for the individual compoundsdisclosed in Tables 1A to 30A, 1B to 29B, 1C to 33C, 1D to 27D or 1E to27E (below), or the individual compounds disclosed in Tables T1a, T1b,T2a, T2b, T3a, T3b, T4a, T4b, T5a or T5b (below).

Compounds of the present invention can be made as shown in the followingschemes, in which, unless otherwise stated, the definition of eachvariable is as defined above for a compound of formula (I).

The compounds of formula (I) can be obtained by an amide couplingtransformation with compounds of formula (A) and compounds of formula(B) by activating the carboxylic acid function of the compounds offormula (A), a process that usually takes place by converting the —OH ofthe carboxylic acid into a good leaving group, such as a chloride group,for example by using (COCl)₂ or SOCl₂, prior to treatment with thecompounds of formula (B), preferably in a suitable solvent (eg,dimethylformamide, dichloromethane or tetrahydrofuran), preferably at atemperature of between 25° C. and 100° C., and optionally in thepresence of a base such as triethyl amine or N,N-diisopropylethylamine,or under conditions described in the literature for an amide coupling.This reaction is shown in Scheme 1 below. For examples, see Valeur, E.;Bradley, M. Chem. Soc. Rev. (2009), 38, 606 and Chinchilla, R., Najera,C. Chem. Soc. Rev. (2011), 40, 5084. Compounds of formula (A) can bemade by known methods from known compounds or are commerciallyavailable. For examples, see: Liu, K. et al. J. Med. Chem. (2008), 51,7843 and WO 2013/008162 A1. Compounds of formula (B) are known compoundsor are commercially available.

Alternatively, compounds of formula (I) can be prepared from compoundsof formula (C) by treatment with trifluoroacetic anhydride (TFAA) in asuitable solvent, such as tetrahydrofuran, at a temperature between 0°C. and 25° C. For related examples, see Kitamura, S. et al. Chem. Pharm.Bull. (2001), 49, 268. This reaction is shown in Scheme 2.

Compounds of formula (C) can be prepared from compounds of formula (D)by treating them with a hydroxylamine hydrochloride salt in the presenceof a base, such as sodium carbonate, in a suitable solvent, such asmethanol, at a temperature between 0° C. and 100° C. For relatedexamples, see Kitamura, S. et al. Chem. Pharm. Bull. (2001), 49, 268.This reaction is shown in Scheme 3.

Compounds of formula (D) are known or may be made by known methods fromknown compounds. See for examples Chobanian, H. R. et al Tet. Lett.(2006), 47, 3303; or Makovec, F. et al J. Med. Chem. (1992), 35, 3633.

Surprisingly, it has now been found that the compounds of formula (I)have, for practical purposes, a very advantageous level of biologicalactivity for protecting plants against diseases that are caused byfungi.

The compounds of formula (I) can be used in the agricultural sector andrelated fields of use, e.g., as active ingredients for controlling plantpests or on non-living materials for control of spoilage microorganismsor organisms potentially harmful to man. The novel compounds aredistinguished by excellent activity at low rates of application, bybeing well tolerated by plants and by being environmentally safe. Theyhave very useful curative, preventive and systemic properties and may beused for protecting numerous cultivated plants. The compounds of formula(I) can be used to inhibit or destroy the pests that occur on plants orparts of plants (fruit, blossoms, leaves, stems, tubers, roots) ofdifferent crops of useful plants, while at the same time protecting alsothose parts of the plants that grow later, e.g., from phytopathogenicmicroorganisms.

The present invention further relates to a method for controlling orpreventing infestation of plants or plant propagation material and/orharvested food crops susceptible to microbial attack by treating plantsor plant propagation material and/or harvested food crops wherein aneffective amount a compound of formula (I) is applied to the plants, toparts thereof or the locus thereof.

The present invention also relates to the use of the compounds offormula (I) as a fungicide. The term “fungicide” as used herein means acompound that controls, modifies, or prevents the growth of fungi. Theterm “fungicidally effective amount” in accordance with presentinvention means the quantity of such a compound or combination of suchcompounds that is capable of producing an effect on the growth of fungi.Controlling or modifying effects include all deviation from naturaldevelopment, such as killing, retardation and the like, and preventionincludes barrier or other defensive formation in or on a plant toprevent fungal infection.

It is also possible to use the compounds of formula (I) as dressingagents for the treatment of plant propagation material, e.g., seed, suchas fruits, tubers or grains, or plant cuttings (eg, rice), for theprotection against fungal infections as well as against phytopathogenicfungi occurring in the soil. The propagation material can be treatedwith a composition comprising a compound of formula (I) before planting:seed, for example, can be dressed before being sown. The activeingredients according to the invention can also be applied to grains(coating), either by impregnating the seeds in a liquid formulation orby coating them with a solid formulation. The composition can also beapplied to the planting site when the propagation material is beingplanted, for example, to the seed furrow during sowing. The inventionrelates also to such methods of treating plant propagation material andto the plant propagation material so treated.

Furthermore, the compounds of formula (I) can be used for controllingfungi in related areas, for example in the protection of technicalmaterials, including wood and wood-related technical products, in foodstorage, in hygiene management.

In addition, the compounds of formula (I) may be used to protectnon-living materials from fungal attack, e.g., lumber, wall boards andpaint.

The compounds of formula (I) are for example, effective against fungiand fungal vectors of disease as well as phytopathogenic bacteria andviruses. These fungi and fungal vectors of disease, as well asphytopathogenic bacteria and viruses are for example:

Absidia corymbifera, Alternaria spp, Aphanomyces spp, Ascochyta spp,Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A.niger, A. terrus, Aureobasidium spp. including A. pullulans, Blastomycesdermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp.including B. dothidea, B. obtusa, Botrytis spp. including B. cinerea,Candida spp. including C. albicans, C. glabrata, C. krusei, C.lusitaniae, C. parapsilosis, C. tropicalis, Cephaloascus fragrans,Ceratocystis spp, Cercospora spp. including C. arachidicola,Cercosporidium personatum, Cladosporium spp, Claviceps purpurea,Coccidioides immitis, Cochliobolus spp, Colletotrichum spp. including C.musae, Cryptococcus neoformans, Diaporthe spp, Didymella spp, Drechsleraspp, Elsinoe spp, Epidermophyton spp, Erwinia amylovora, Erysiphe spp.including E. cichoracearum, Eutypa lata, Fusarium spp. including F.culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum,F. proliferatum, F. subglutinans, F. solani, Gaeumannomyces graminis,Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum,Glomerella cingulate, Guignardia bidwellii, Gymnosporangiumjuniperi-virginianae, Helminthosporium spp, Hemileia spp, Histoplasmaspp. including H. capsulatum, Laetisaria fuciformis, Leptographiumlindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochiumnivale, Microsporum spp, Monilinia spp, Mucor spp, Mycosphaerella spp.including M. graminicola, M. pomi, Oncobasidium theobromaeon, Ophiostomapiceae, Paracoccidioides spp, Penicillium spp. including P. digitatum,P. italicum, Petriellidium spp, Peronosclerospora spp. Including P.maydis, P. philippinensis and P. sorghi, Peronospora spp, Phaeosphaerianodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp,Phoma spp, Phomopsis viticola, Phytophthora spp. including P. infestans,Plasmopara spp. including P. halstedii, P. viticola, Pleospora spp.,Podosphaera spp. including P. leucotricha, Polymyxa graminis, Polymyxabetae, Pseudocercosporella herpotrichoides, Pseudomonas spp,Pseudoperonospora spp. including P. cubensis, P. humuli, Pseudopezizatracheiphila, Puccinia Spp. including P. hordei, P. recondita, P.striiformis, P. triticina, Pyrenopeziza spp, Pyrenophora spp,Pyricularia spp. including P. oryzae, Pythium spp. including P. ultimum,Ramularia spp, Rhizoctonia spp, Rhizomucor pusillus, Rhizopus arrhizus,Rhynchosporium spp, Scedosporium spp. including S. apiospermum and S.prolificans, Schizothyrium pomi, Sclerotinia spp, Sclerotium spp,Septoria spp, including S. nodorum, S. tritici, Sphaerotheca macularis,Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp,Stagonospora nodorum, Stemphylium spp, Stereum hirsutum, Thanatephoruscucumeris, Thielaviopsis basicola, Tilletia spp, Trichoderma spp.including T. harzianum, T. pseudokoningii, T. viride, Trichophyton spp,Typhula spp, Uncinula necator, Urocystis spp, Ustilago spp, Venturiaspp. including V. inaequalis, Verticillium spp, and Xanthomonas spp.

Within the scope of present invention, target crops and/or useful plantsto be protected typically comprise perennial and annual crops, such asberry plants for example blackberries, blueberries, cranberries,raspberries and strawberries; cereals for example barley, maize (corn),millet, oats, rice, rye, sorghum triticale and wheat; fibre plants forexample cotton, flax, hemp, jute and sisal; field crops for examplesugar and fodder beet, coffee, hops, mustard, oilseed rape (canola),poppy, sugar cane, sunflower, tea and tobacco; fruit trees for exampleapple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pearand plum; grasses for example Bermuda grass, bluegrass, bentgrass,centipede grass, fescue, ryegrass, St. Augustine grass and Zoysia grass;herbs such as basil, borage, chives, coriander, lavender, lovage, mint,oregano, parsley, rosemary, sage and thyme; legumes for example beans,lentils, peas and soya beans; nuts for example almond, cashew, groundnut, hazelnut, peanut, pecan, pistachio and walnut; palms for exampleoil palm; ornamentals for example flowers, shrubs and trees; othertrees, for example cacao, coconut, olive and rubber; vegetables forexample asparagus, aubergine, broccoli, cabbage, carrot, cucumber,garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin,rhubarb, spinach and tomato; and vines for example grapes.

The term “useful plants” is to be understood as including also usefulplants that have been rendered tolerant to herbicides like bromoxynil orclasses of herbicides (such as, for example, HPPD inhibitors, ALSinhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron,EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS(glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase)inhibitors) as a result of conventional methods of breeding or geneticengineering. An example of a crop that has been rendered tolerant toimidazolinones, e.g. imazamox, by conventional methods of breeding(mutagenesis) is Clearfield® summer rape (Canola). Examples of cropsthat have been rendered tolerant to herbicides or classes of herbicidesby genetic engineering methods include glyphosate- andglufosinate-resistant maize varieties commercially available under thetrade names RoundupReady®, Herculex I® and LibertyLink®.

The term “useful plants” is to be understood as including also usefulplants which have been so transformed by the use of recombinant DNAtechniques that they are capable of synthesising one or more selectivelyacting toxins, such as are known, for example, from toxin-producingbacteria, especially those of the genus Bacillus.

Examples of such plants are: YieldGard® (maize variety that expresses aCryIA(b) toxin); YieldGard Rootworm® (maize variety that expresses aCryIIIB(b1) toxin); YieldGard Plus® (maize variety that expresses aCryIA(b) and a CryIIIB(b1) toxin); Starlink® (maize variety thatexpresses a Cry9(c) toxin); Herculex I® (maize variety that expresses aCryIF(a2) toxin and the enzyme phosphinothricine N-acetyltransferase(PAT) to achieve tolerance to the herbicide glufosinate ammonium);NuCOTN 33B® (cotton variety that expresses a CryIA(c) toxin); BollgardI® (cotton variety that expresses a CryIA(c) toxin); Bollgard II®(cotton variety that expresses a CryIA(c) and a CryIIA(b) toxin);VIPCOT® (cotton variety that expresses a VIP toxin); NewLeaf® (potatovariety that expresses a CryIIIA toxin); NatureGard® Agrisure® GTAdvantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt11corn borer (CB) trait), Agrisure® RW (corn rootworm trait) andProtecta®.

The term “crops” is to be understood as including also crop plants whichhave been so transformed by the use of recombinant DNA techniques thatthey are capable of synthesising one or more selectively acting toxins,such as are known, for example, from toxin-producing bacteria,especially those of the genus Bacillus.

Toxins that can be expressed by such transgenic plants include, forexample, insecticidal proteins from Bacillus cereus or Bacilluspopilliae; or insecticidal proteins from Bacillus thuringiensis, such as8-endotoxins, e.g. Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A,Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1,Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonisingnematodes, for example Photorhabdus spp. or Xenorhabdus spp., such asPhotorhabdus luminescens, Xenorhabdus nematophilus; toxins produced byanimals, such as scorpion toxins, arachnid toxins, wasp toxins and otherinsect-specific neurotoxins; toxins produced by fungi, such asStreptomycetes toxins, plant lectins, such as pea lectins, barleylectins or snowdrop lectins; agglutinins; proteinase inhibitors, such astrypsin inhibitors, serine protease inhibitors, patatin, cystatin,papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin,maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolismenzymes, such as 3-hydroxysteroidoxidase,ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidases, ecdysoneinhibitors, HMG-COA-reductase, ion channel blockers, such as blockers ofsodium or calcium channels, juvenile hormone esterase, diuretic hormonereceptors, stilbene synthase, bibenzyl synthase, chitinases andglucanases.

In the context of the present invention there are to be understood by8-endotoxins, for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A,Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for exampleVip1, Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncatedtoxins and modified toxins. Hybrid toxins are produced recombinantly bya new combination of different domains of those proteins (see, forexample, WO 02/15701). Truncated toxins, for example a truncated Cry1Ab,are known. In the case of modified toxins, one or more amino acids ofthe naturally occurring toxin are replaced. In such amino acidreplacements, preferably non-naturally present protease recognitionsequences are inserted into the toxin, such as, for example, in the caseof Cry3A055, a cathepsin-G-recognition sequence is inserted into a Cry3Atoxin (see WO 03/018810).

Examples of such toxins or transgenic plants capable of synthesisingsuch toxins are disclosed, for example, in EP-A-0 374 753, WO 93/07278,WO 95/34656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073.

The processes for the preparation of such transgenic plants aregenerally known to the person skilled in the art and are described, forexample, in the publications mentioned above. Cryl-type deoxyribonucleicacids and their preparation are known, for example, from WO 95/34656,EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.

The toxin contained in the transgenic plants imparts to the plantstolerance to harmful insects. Such insects can occur in any taxonomicgroup of insects, but are especially commonly found in the beetles(Coleoptera), two-winged insects (Diptera) and butterflies(Lepidoptera).

Transgenic plants containing one or more genes that code for aninsecticidal resistance and express one or more toxins are known andsome of them are commercially available. Examples of such plants are:YieldGard® (maize variety that expresses a Cry1Ab toxin); YieldGardRootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGardPlus® (maize variety that expresses a Cry1Ab and a Cry3Bb1 toxin);Starlink® (maize variety that expresses a Cry9C toxin); Herculex I®(maize variety that expresses a Cry1Fa2 toxin and the enzymephosphinothricine N-acetyltransferase (PAT) to achieve tolerance to theherbicide glufosinate ammonium); NuCOTN 33B® (cotton variety thatexpresses a Cry1Ac toxin); Bollgard I® (cotton variety that expresses aCry1Ac toxin); Bollgard II® (cotton variety that expresses a Cry1Ac anda Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A and aCry1Ab toxin); NewLeaf® (potato variety that expresses a Cry3A toxin);NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait),Agrisure® CB Advantage (Bt11 corn borer (CB) trait) and Protecta®.

Further examples of such transgenic crops are:

1. Bt11 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Geneticallymodified Zea mays which has been rendered resistant to attack by theEuropean corn borer (Ostrinia nubilalis and Sesamia nonagrioides) bytransgenic expression of a truncated Cry1Ab toxin. Bt11 maize alsotransgenically expresses the enzyme PAT to achieve tolerance to theherbicide glufosinate ammonium.2. Bt176 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Geneticallymodified Zea mays which has been rendered resistant to attack by theEuropean corn borer (Ostrinia nubilalis and Sesamia nonagrioides) bytransgenic expression of a Cry1Ab toxin. Bt176 maize also transgenicallyexpresses the enzyme PAT to achieve tolerance to the herbicideglufosinate ammonium.3. MIR604 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Maize which hasbeen rendered insect-resistant by transgenic expression of a modifiedCry3A toxin. This toxin is Cry3A055 modified by insertion of acathepsin-G-protease recognition sequence. The preparation of suchtransgenic maize plants is described in WO 03/018810.4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren,B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863expresses a Cry3Bb1 toxin and has resistance to certain Coleopterainsects.5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren,B-1150 Brussels, Belgium, registration number C/ES/96/02.6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7B-1160 Brussels, Belgium, registration number C/NL/00/10. Geneticallymodified maize for the expression of the protein CryIF for achievingresistance to certain Lepidoptera insects and of the PAT protein forachieving tolerance to the herbicide glufosinate ammonium.7. NK603×MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue deTervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03.Consists of conventionally bred hybrid maize varieties by crossing thegenetically modified varieties NK603 and MON 810. NK603×MON 810 Maizetransgenically expresses the protein CP4 EPSPS, obtained fromAgrobacterium sp. strain CP4, which imparts tolerance to the herbicideRoundup® (contains glyphosate), and also a Cry1Ab toxin obtained fromBacillus thuringiensis subsp. kurstaki which brings about tolerance tocertain Lepidoptera, include the European corn borer.

The term “locus” as used herein means fields in or on which plants aregrowing, or where seeds of cultivated plants are sown, or where seedwill be placed into the soil. It includes soil, seeds, and seedlings, aswell as established vegetation.

The term “plants” refers to all physical parts of a plant, includingseeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, andfruits.

The term “plant propagation material” is understood to denote generativeparts of the plant, such as seeds, which can be used for themultiplication of the latter, and vegetative material, such as cuttingsor tubers, for example potatoes. There may be mentioned for exampleseeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes andparts of plants. Germinated plants and young plants which are to betransplanted after germination or after emergence from the soil, mayalso be mentioned. These young plants may be protected beforetransplantation by a total or partial treatment by immersion.Preferably, “plant propagation material” is understood to denote seeds.

The compounds of formula (I) may be used in unmodified form or,preferably, together with the adjuvants conventionally employed in theart of formulation. To this end they may be conveniently formulated inknown manner to emulsifiable concentrates, coatable pastes, directlysprayable or dilutable solutions or suspensions, dilute emulsions,wettable powders, soluble powders, dusts, granulates, and alsoencapsulations, e.g., in polymeric substances. As with the type of thecompositions, the methods of application, such as spraying, atomising,dusting, scattering, coating or pouring, are chosen in accordance withthe intended objectives and the prevailing circumstances. Thecompositions may also contain further adjuvants such as stabilizers,antifoams, viscosity regulators, binders or tackifiers as well asfertilizers, micronutrient donors or other formulations for obtainingspecial effects.

Suitable carriers and adjuvants, e.g., for agricultural use, can besolid or liquid and are substances useful in formulation technology,e.g. natural or regenerated mineral substances, solvents, dispersants,wetting agents, tackifiers, thickeners, binders or fertilizers. Suchcarriers are for example described in WO 97/33890.

Suspension concentrates are aqueous formulations in which finely dividedsolid particles of the active compound are suspended. Such formulationsinclude anti-settling agents and dispersing agents and may furtherinclude a wetting agent to enhance activity as well an anti-foam and acrystal growth inhibitor. In use, these concentrates are diluted inwater and normally applied as a spray to the area to be treated. Theamount of active ingredient may range from 0.5% to 95% of theconcentrate.

Wettable powders are in the form of finely divided particles whichdisperse readily in water or other liquid carriers. The particlescontain the active ingredient retained in a solid matrix. Typical solidmatrices include fuller's earth, kaolin clays, silicas and other readilywet organic or inorganic solids. Wettable powders normally contain from5% to 95% of the active ingredient plus a small amount of wetting,dispersing or emulsifying agent.

Emulsifiable concentrates are homogeneous liquid compositionsdispersible in water or other liquid and may consist entirely of theactive compound with a liquid or solid emulsifying agent, or may alsocontain a liquid carrier, such as xylene, heavy aromatic naphthas,isophorone and other non-volatile organic solvents. In use, theseconcentrates are dispersed in water or other liquid and normally appliedas a spray to the area to be treated. The amount of active ingredientmay range from 0.5% to 95% of the concentrate.

Granular formulations include both extrudates and relatively coarseparticles and are usually applied without dilution to the area in whichtreatment is required. Typical carriers for granular formulationsinclude sand, fuller's earth, attapulgite clay, bentonite clays,montmorillonite clay, vermiculite, perlite, calcium carbonate, brick,pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, ground corncobs, ground peanut hulls, sugars, sodium chloride, sodium sulphate,sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide,titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth,calcium sulphate and other organic or inorganic materials which absorbor which can be coated with the active compound. Granular formulationsnormally contain 5% to 25% of active ingredients which may includesurface-active agents such as heavy aromatic naphthas, kerosene andother petroleum fractions, or vegetable oils; and/or stickers such asdextrins, glue or synthetic resins.

Dusts are free-flowing admixtures of the active ingredient with finelydivided solids such as talc, clays, flours and other organic andinorganic solids which act as dispersants and carriers.

Microcapsules are typically droplets or granules of the activeingredient enclosed in an inert porous shell which allows escape of theenclosed material to the surroundings at controlled rates. Encapsulateddroplets are typically 1 to 50 microns in diameter. The enclosed liquidtypically constitutes 50 to 95% of the weight of the capsule and mayinclude solvent in addition to the active compound. Encapsulatedgranules are generally porous granules with porous membranes sealing thegranule pore openings, retaining the active species in liquid forminside the granule pores. Granules typically range from 1 millimetre to1 centimetre and preferably 1 to 2 millimetres in diameter. Granules areformed by extrusion, agglomeration or prilling, or are naturallyoccurring. Examples of such materials are vermiculite, sintered clay,kaolin, attapulgite clay, sawdust and granular carbon. Shell or membranematerials include natural and synthetic rubbers, cellulosic materials,styrene-butadiene copolymers, polyacrylonitriles, polyacrylates,polyesters, polyamides, polyureas, polyurethanes and starch xanthates.

Other useful formulations for agrochemical applications include simplesolutions of the active ingredient in a solvent in which it iscompletely soluble at the desired concentration, such as acetone,alkylated naphthalenes, xylene and other organic solvents. Pressurisedsprayers, wherein the active ingredient is dispersed in finely-dividedform as a result of vaporisation of a low boiling dispersant solventcarrier, may also be used.

Suitable agricultural adjuvants and carriers that are useful informulating the compositions of the invention in the formulation typesdescribed above are well known to those skilled in the art.

Liquid carriers that can be employed include, for example, water,toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethylketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone,amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol,alkyl acetates, diacetonalcohol, 1,2-dichloropropane, diethanolamine,p-diethylbenzene, diethylene glycol, diethylene glycol abietate,diethylene glycol butyl ether, diethylene glycol ethyl ether, diethyleneglycol methyl ether, N,N-dimethyl formamide, dimethyl sulfoxide,1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether,dipropylene glycol dibenzoate, diproxitol, alkyl pyrrolidinone, ethylacetate, 2-ethyl hexanol, ethylene carbonate, 1,1,1-trichloroethane,2-heptanone, alpha pinene, d-limonene, ethylene glycol, ethylene glycolbutyl ether, ethylene glycol methyl ether, gamma-butyrolactone,glycerol, glycerol diacetate, glycerol monoacetate, glycerol triacetate,hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate,isooctane, isophorone, isopropyl benzene, isopropyl myristate, lacticacid, laurylamine, mesityl oxide, methoxy-propanol, methyl isoamylketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyloleate, methylene chloride, m-xylene, n-hexane, n-octylamine,octadecanoic acid, octyl amine acetate, oleic acid, oleylamine,o-xylene, phenol, polyethylene glycol (PEG400), propionic acid,propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene,triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin,mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amylacetate, butyl acetate, methanol, ethanol, isopropanol, and highermolecular weight alcohols such as amyl alcohol, tetrahydrofurfurylalcohol, hexanol, octanol, etc., ethylene glycol, propylene glycol,glycerine and N-methyl-2-pyrrolidinone. Water is generally the carrierof choice for the dilution of concentrates.

Suitable solid carriers include, for example, talc, titanium dioxide,pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk,diatomaxeous earth, lime, calcium carbonate, bentonite clay, fuller'searth, cotton seed hulls, wheat flour, soybean flour, pumice, woodflour, walnut shell flour and lignin.

A broad range of surface-active agents are advantageously employed inboth said liquid and solid compositions, especially those designed to bediluted with carrier before application. These agents, when used,normally comprise from 0.1% to 15% by weight of the formulation. Theycan be anionic, cationic, non-ionic or polymeric in character and can beemployed as emulsifying agents, wetting agents, suspending agents or forother purposes. Typical surface active agents include salts of alkylsulfates, such as diethanolammonium lauryl sulphate; alkylarylsulfonatesalts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkyleneoxide addition products, such as nonylphenol-C.sub. 18 ethoxylate;alcohol-alkylene oxide addition products, such as tridecylalcohol-C.sub. 16 ethoxylate; soaps, such as sodium stearate;alkylnaphthalenesulfonate salts, such as sodiumdibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts,such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such assorbitol oleate; quaternary amines, such as lauryl trimethylammoniumchloride; polyethylene glycol esters of fatty acids, such aspolyethylene glycol stearate; block copolymers of ethylene oxide andpropylene oxide; and salts of mono and dialkyl phosphate esters.

Other adjuvants commonly utilized in agricultural compositions includecrystallisation inhibitors, viscosity modifiers, suspending agents,spray droplet modifiers, pigments, antioxidants, foaming agents,anti-foaming agents, light-blocking agents, compatibilizing agents,antifoam agents, sequestering agents, neutralising agents and buffers,corrosion inhibitors, dyes, odorants, spreading agents, penetrationaids, micronutrients, emollients, lubricants and sticking agents.

In addition, further, other biocidally active ingredients orcompositions may be combined with the compositions of the invention andused in the methods of the invention and applied simultaneously orsequentially with the compositions of the invention. When appliedsimultaneously, these further active ingredients may be formulatedtogether with the compositions of the invention or mixed in, forexample, the spray tank. These further biocidally active ingredients maybe fungicides, herbicides, insecticides, bactericides, acaricides,nematicides and/or plant growth regulators.

Pesticidal agents are referred to herein using their common name areknown, for example, from “The Pesticide Manual”, 15th Ed., British CropProtection Council 2009.

In addition, the compositions of the invention may also be applied withone or more systemically acquired resistance inducers (“SAR” inducer).SAR inducers are known and described in, for example, U.S. Pat. No.6,919,298 and include, for example, salicylates and the commercial SARinducer acibenzolar-S-methyl.

The compounds of formula (I) are normally used in the form ofcompositions and can be applied to the crop area or plant to be treated,simultaneously or in succession with further compounds. These furthercompounds can be e.g. fertilizers or micronutrient donors or otherpreparations, which influence the growth of plants. They can also beselective herbicides or non-selective herbicides as well asinsecticides, fungicides, bactericides, nematicides, molluscicides ormixtures of several of these preparations, if desired together withfurther carriers, surfactants or application promoting adjuvantscustomarily employed in the art of formulation.

The compounds of formula (I) may be used in the form of (fungicidal)compositions for controlling or protecting against phytopathogenicmicroorganisms, comprising as active ingredient at least one compound offormula (I) or of at least one preferred individual compound asabove-defined, in free form or in agrochemically usable salt form, andat least one of the above-mentioned adjuvants.

The invention, in particular as it relates to the compounds of Formula(I) (including Formulae (IA), (IB), (IC), (ID) and (IE)), provides acomposition, preferably a fungicidal composition, comprising at leastone compound formula (I), an agriculturally acceptable carrier andoptionally an adjuvant. An agricultural acceptable carrier is forexample a carrier that is suitable for agricultural use. Agriculturalcarriers are well known in the art. Preferably, said composition maycomprise at least one or more pesticidally active compounds, for examplean additional fungicidal active ingredient in addition to the compoundof formula (I).

The compound of formula (I) may be the sole active ingredient of acomposition or it may be admixed with one or more additional activeingredients such as a pesticide, fungicide, synergist, herbicide orplant growth regulator where appropriate. An additional activeingredient may, in some cases, result in unexpected synergisticactivities.

Examples of suitable additional active ingredients include the followingacycloamino acid fungicides, aliphatic nitrogen fungicides, amidefungicides, anilide fungicides, antibiotic fungicides, aromaticfungicides, arsenical fungicides, aryl phenyl ketone fungicides,benzamide fungicides, benzanilide fungicides, benzimidazole fungicides,benzothiazole fungicides, botanical fungicides, bridged diphenylfungicides, carbamate fungicides, carbanilate fungicides, conazolefungicides, copper fungicides, dicarboximide fungicides, dinitrophenolfungicides, dithiocarbamate fungicides, dithiolane fungicides, furamidefungicides, furanilide fungicides, hydrazide fungicides, imidazolefungicides, mercury fungicides, morpholine fungicides, organophosphorousfungicides, organotin fungicides, oxathiin fungicides, oxazolefungicides, phenylsulfamide fungicides, polysulfide fungicides, pyrazolefungicides, pyridine fungicides, pyrimidine fungicides, pyrrolefungicides, quaternary ammonium fungicides, quinoline fungicides,quinone fungicides, quinoxaline fungicides, strobilurin fungicides,sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides,thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides,triazine fungicides, triazole fungicides, triazolopyrimidine fungicides,urea fungicides, valinamide fungicides, and zinc fungicides.

Examples of suitable additional active ingredients also include thefollowing: 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid(9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide,3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acidmethoxy-[1-methyl-2-(2,4,6-trichlorophenyl)-ethyl]-amide,1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid(2-dichloromethylene-3-ethyl-1-methyl-indan-4-yl)-amide (1072957-71-1),1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid(4′-methylsulfanyl-biphenyl-2-yl)-amide,1-methyl-3-difluoromethyl-4H-pyrazole-4-carboxylic acid[2-(2,4-dichloro-phenyl)-2-methoxy-1-methyl-ethyl]-amide,(5-Chloro-2,4-dimethyl-pyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone,(5-Bromo-4-chloro-2-methoxy-pyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone,2-{2-[(E)-3-(2,6-Dichloro-phenyl)-1-methyl-prop-2-en-(E)-ylideneaminooxymethyl]-phenyl}-2-[(Z)-methoxyimino]-N-methyl-acetamide,3-[5-(4-Chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine,(E)-N-methyl-2-[2-(2, 5-dimethylphenoxymethyl)phenyl]-2-methoxy-iminoacetamide, 4-bromo-2-cyano-N,N-dimethyl-6-trifluoromethylbenzimidazole-1-sulphonamide,a-[N-(3-chloro-2, 6-xylyl)-2-methoxyacetamido]-y-butyrolactone,4-chloro-2-cyano-N,-dimethyl-5-p-tolylimidazole-1-sulfonamide,N-allyl-4, 5,-dimethyl-2-trimethylsilylthiophene-3-carboxamide,N-(I-cyano-1, 2-dimethylpropyl)-2-(2, 4-dichlorophenoxy) propionamide,N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide,(.+−.)-cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,2-(1-tert-butyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)-propan-2-ol,2′,6′-dibromo-2-methyl-4-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanilide,1-imidazolyl-1-(4′-chlorophenoxy)-3,3-dimethylbutan-2-one, methyl(E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]3-methoxyacrylate,methyl(E)-2-[2-[6-(2-thioamidophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2-fluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2,6-difluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl (E)-2-[2-[3-(pyrimidin-2-yloxy)phenoxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[3-(5-methylpyrimidin-2-yloxy)-phenoxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[3-(phenyl-sulphonyloxy)phenoxy]phenyl-3-methoxyacrylate,methyl (E)-2-[2-[3-(4-nitrophenoxy)phenoxy]phenyl]-3-methoxyacrylate,methyl (E)-2-[2-phenoxyphenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3,5-dimethyl-benzoyl)pyrrol-1-yl]-3-methoxyacrylate, methyl(E)-2-[2-(3-methoxyphenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(2-phenylethen-1-yl)-phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3,5-dichlorophenoxy)pyridin-3-yl]-3-methoxyacrylate, methyl(E)-2-(2-(3-(1,1,2,2-tetrafluoroethoxy)phenoxy)phenyl)-3-methoxyacrylate,methyl(E)-2-(2-[3-(alpha-hydroxybenzyl)phenoxy]phenyl)-3-methoxyacrylate,methyl (E)-2-(2-(4-phenoxypyridin-2-yloxy)phenyl)-3-methoxyacrylate,methyl (E)-2-[2-(3-n-propyloxy-phenoxy)phenyl]3-methoxyacrylate, methyl(E)-2-[2-(3-isopropyloxyphenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[3-(2-fluorophenoxy)phenoxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3-ethoxyphenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(4-tert-butyl-pyridin-2-yloxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[3-(3-cyanophenoxy)phenoxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[(3-methyl-pyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2-methyl-phenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-(5-bromo-pyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate,methyl(E)-2-[2-(3-(3-iodopyridin-2-yloxy)phenoxy)phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2-chloropyridin-3-yloxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl (E),(E)-2-[2-(5,6-dimethylpyrazin-2-ylmethyloximinomethyl)phenyl]-3-methoxyacrylate, methyl(E)-2-{2-[6-(6-methylpyridin-2-yloxy)pyrimidin-4-yloxy]phenyl}-3-methoxy-acrylate,methyl(E),(E)-2-{2-(3-methoxyphenyl)methyloximinomethyl]-phenyl}-3-methoxyacrylate,methyl(E)-2-{2-(6-(2-azidophenoxy)-pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate,methyl(E),(E)-2-{2-[6-phenylpyrimidin-4-yl)-methyloximinomethyl]phenyl}-3-methoxyacrylate,methyl(E),(E)-2-{2-[(4-chlorophenyl)-methyloximinomethyl]-phenyl}-3-methoxyacrylate,methyl(E)-2-{2-[6-(2-n-propylphenoxy)-1,3,5-triazin-4-yloxy]phenyl}-3-methoxyacrylate,methyl(E),(E)-2-{2-[(3-nitrophenyl)methyloximinomethyl]phenyl}-3-methoxyacrylate,3-chloro-7-(2-aza-2,7,7-trimethyl-oct-3-en-5-ine),2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide, 3-iodo-2-propinylalcohol, 4-chlorophenyl-3-iodopropargyl formal,3-bromo-2,3-diiodo-2-propenyl ethylcarbamate, 2,3,3-triiodoallylalcohol, 3-bromo-2,3-diiodo-2-propenyl alcohol, 3-iodo-2-propinyln-butylcarbamate, 3-iodo-2-propinyl n-hexylcarbamate, 3-iodo-2-propinylcyclohexyl-carbamate, 3-iodo-2-propinyl phenylcarbamate; phenolderivatives, such as tribromophenol, tetrachlorophenol,3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol,dichlorophene, o-phenylphenol, m-phenylphenol, p-phenylphenol,2-benzyl-4-chlorophenol, 5-hydroxy-2-(5H)-furanone;4,5-dichlorodithiazolinone, 4,5-benzodithiazolinone,4,5-trimethylenedithiazolinone, 4,5-dichloro-(3H)-1,2-dithiol-3-one,3,5-dimethyl-tetrahydro-1,3,5-thiadiazine-2-thione,N-(2-p-chlorobenzoylethyl)-hexaminium chloride, acibenzolar, acypetacs,alanycarb, albendazole, aldimorph, allicin, allyl alcohol, ametoctradin,amisulbrom, amobam, ampropylfos, anilazine, asomate, aureofungin,azaconazole, azafendin, azithiram, azoxystrobin, barium polysulfide,benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentaluron,benthiavalicarb, benthiazole, benzalkonium chloride, benzamacril,benzamorf, benzohydroxamic acid, berberine, bethoxazin, biloxazol,binapacryl, biphenyl, bitertanol, bithionol, bixafen, blasticidin-S,boscalid, bromothalonil, bromuconazole, bupirimate, buthiobate,butylamine calcium polysulfide, captafol, captan, carbamorph,carbendazim, carbendazim chlorhydrate, carboxin, carpropamid, carvone,CGA41396, CGA41397, chinomethionate, chitosan, chlobenthiazone,chloraniformethan, chloranil, chlorfenazole, chloroneb, chloropicrin,chlorothalonil, chlorozolinate, chlozolinate, climbazole, clotrimazole,clozylacon, copper containing compounds such as copper acetate, coppercarbonate, copper hydroxide, copper naphthenate, copper oleate, copperoxychloride, copper oxyquinolate, copper silicate, copper sulphate,copper tallate, copper zinc chromate and Bordeaux mixture, cresol,cufraneb, cuprobam, cuprous oxide, cyazofamid, cyclafuramid,cycloheximide, cyflufenamid, cymoxanil, cypendazole, cyproconazole,cyprodinil, dazomet, debacarb, decafentin, dehydroacetic acid,di-2-pyridyl disulphide 1, 1′-dioxide, dichlofluanid, diclomezine,dichlone, dicloran, dichlorophen, dichlozoline, diclobutrazol,diclocymet, diethofencarb, difenoconazole, difenzoquat, diflumetorim, O,O-di-iso-propyl-S-benzyl thiophosphate, dimefluazole, dimetachlone,dimetconazole, dimethomorph, dimethirimol, diniconazole, diniconazole-M,dinobuton, dinocap, dinocton, dinopenton, dinosulfon, dinoterbon,diphenylamine, dipyrithione, disulfiram, ditalimfos, dithianon,dithioether, dodecyl dimethyl ammonium chloride, dodemorph, dodicin,dodine, doguadine, drazoxolon, edifenphos, enestroburin, epoxiconazole,etaconazole, etem, ethaboxam, ethirimol, ethoxyquin, ethilicin, ethyl(Z)-N-benzyl-N ([methyl (methyl-thioethylideneamino-oxycarbonyl) amino]thio)-β-alaninate, etridiazole, famoxadone, fenamidone, fenaminosulf,fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan,fenoxanil, fenpiclonil, fenpropidin, fenpropimorph, fenpyrazamine,fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam,fludioxonil, flumetover, flumorph, flupicolide, fluopyram, fluoroimide,fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole,flusulfamide, flutanil, flutolanil, flutriafol, fluxapyroxad, folpet,formaldehyde, fosetyl, fuberidazole, furalaxyl, furametpyr, furcarbanil,furconazole, furfural, furmecyclox, furophanate, glyodin, griseofulvin,guazatine, halacrinate, hexa chlorobenzene, hexachlorobutadiene,hexachlorophene, hexaconazole, hexylthiofos, hydrargaphen,hydroxyisoxazole, hymexazole, imazalil, imazalil sulphate,imibenconazole, iminoctadine, iminoctadine triacetate, inezin, iodocarb,ipconazole, iprobenfos, iprodione, iprovalicarb, isopropanyl butylcarbamate, isoprothiolane, isopyrazam, isotianil, isovaledione,izopamfos, kasugamycin, kresoxim-methyl, LY186054, LY211795, LY248908,mancozeb, mandipropamid, maneb, mebenil, mecarbinzid, mefenoxam,mepanipyrim, mepronil, mercuric chloride, mercurous chloride,meptyldinocap, metalaxyl, metalaxyl-M, metam, metazoxolon, metconazole,methasulfocarb, methfuroxam, methyl bromide, methyl iodide, methylisothiocyanate, metiram, metiram-zinc, metominostrobin, metrafenone,metsulfovax, milneb, moroxydine, myclobutanil, myclozolin, nabam,natamycin, neoasozin, nickel dimethyldithiocarbamate, nitrostyrene,nitrothal-iso-propyl, nuarimol, octhilinone, ofurace, organomercurycompounds, orysastrobin, osthol, oxadixyl, oxasulfuron, oxine-copper,oxolinic acid, oxpoconazole, oxycarboxin, parinol, pefurazoate,penconazole, pencycuron, penflufen, pentachlorophenol, penthiopyrad,phenamacril, phenazin oxide, phosdiphen, phosetyl-AI, phosphorus acids,phthalide, picoxystrobin, piperalin, polycarbamate, polyoxin D,polyoxrim, polyram, probenazole, prochloraz, procymidone, propamidine,propamocarb, propiconazole, propineb, propionic acid, proquinazid,prothiocarb, prothioconazole, pyracarbolid, pyraclostrobin,pyrametrostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyridinitril,pyrifenox, pyrimethanil, pyriofenone, pyroquilon, pyroxychlor,pyroxyfur, pyrrolnitrin, quaternary ammonium compounds, quinacetol,quinazamid, quinconazole, quinomethionate, quinoxyfen, quintozene,rabenzazole, santonin, sedaxane, silthiofam, simeconazole, sipconazole,sodium pentachlorophenate, solatenol, spiroxamine, streptomycin,sulphur, sultropen, tebuconazole, tebfloquin, tecloftalam, tecnazene,tecoram, tetraconazole, thiabendazole, thiadifluor, thicyofen,thifluzamide, 2-(thiocyanomethylthio) benzothiazole, thiophanate-methyl,thioquinox, thiram, tiadinil, timibenconazole, tioxymid,tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triamiphos,triarimol, triazbutil, triazoxide, tricyclazole, tridemorph,trifloxystrobin, triflumazole, triforine, triflumizole, triticonazole,uniconazole, urbacide, validamycin, valifenalate, vapam, vinclozolin,zarilamid, zineb, ziram, and zoxamide.

The compounds of the invention may also be used in combination withanthelmintic agents. Such anthelmintic agents include, compoundsselected from the macrocyclic lactone class of compounds such asivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin,selamectin, moxidectin, nemadectin and milbemycin derivatives asdescribed in EP-357460, EP-444964 and EP-594291. Additional anthelminticagents include semisynthetic and biosynthetic avermectin/milbemycinderivatives such as those described in U.S. Pat. No. 5,015,630,WO-9415944 and WO-9522552. Additional anthelmintic agents include thebenzimidazoles such as albendazole, cambendazole, fenbendazole,flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, andother members of the class. Additional anthelmintic agents includeimidazothiazoles and tetrahydropyrimidines such as tetramisole,levamisole, pyrantel pamoate, oxantel or morantel. Additionalanthelmintic agents include flukicides, such as triclabendazole andclorsulon and the cestocides, such as praziquantel and epsiprantel.

The compounds of the invention may be used in combination withderivatives and analogues of the paraherquamide/marcfortine class ofanthelmintic agents, as well as the antiparasitic oxazolines such asthose disclosed in U.S. Pat. Nos. 5,478,855, 4,639,771 and DE-19520936.

The compounds of the invention may be used in combination withderivatives and analogues of the general class of dioxomorpholineantiparasitic agents as described in WO 96/15121 and also withanthelmintic active cyclic depsipeptides such as those described in WO96/11945, WO 93/19053, WO 93/25543, EP 626375, EP 382173, WO 94/19334,EP 382173, and EP 503538.

The compounds of the invention may be used in combination with otherectoparasiticides; for example, fipronil; pyrethroids; organophosphates;insect growth regulators such as lufenuron; ecdysone agonists such astebufenozide and the like; neonicotinoids such as imidacloprid and thelike.

The compounds of the invention may be used in combination with terpenealkaloids, for example those described in International PatentApplication Publication Numbers WO 95/19363 or WO 04/72086, particularlythe compounds disclosed therein.

Other examples of such biologically active compounds that the compoundsof the invention may be used in combination with include but are notrestricted to the following:

Organophosphates: acephate, azamethiphos, azinphos-ethyl,azinphos-methyl, bromophos, bromophos-ethyl, cadusafos, chlorethoxyphos,chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton-S-methyl,demeton-S-methyl sulphone, dialifos, diazinon, dichlorvos, dicrotophos,dimethoate, disulfoton, ethion, ethoprophos, etrimfos, famphur,fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos,fonofos, formothion, fosthiazate, heptenophos, isazophos, isothioate,isoxathion, malathion, methacriphos, methamidophos, methidathion,methyl-parathion, mevinphos, monocrotophos, naled, omethoate,oxydemeton-methyl, paraoxon, parathion, parathion-methyl, phenthoate,phosalone, phosfolan, phosphocarb, phosmet, phosphamidon, phorate,phoxim, pirimiphos, pirimiphos-methyl, profenofos, propaphos,proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos,sulprophos, temephos, terbufos, tebupirimfos, tetrachlorvinphos,thimeton, triazophos, trichlorfon, vamidothion.

Carbamates: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate,benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb,ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801,isoprocarb, indoxacarb, methiocarb, methomyl,5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb,propoxur, thiodicarb, thiofanox, triazamate, UC-51717.

Pyrethroids: acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl(E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate,bifenthrin, beta-cyfluthrin, cyfluthrin, a-cypermethrin,beta-cypermethrin, bioallethrin, bioallethrin((S)-cyclopentylisomer),bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin,cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate,ethofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate,flumethrin, fluvalinate (D-isomer), imiprothrin, cyhalothrin,lambda-cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrins(natural products), resmethrin, tetramethrin, transfluthrin,theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin,tralomethrin, Zeta-cypermethrin.

Arthropod growth regulators: a) chitin synthesis inhibitors:benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron,flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron,triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole,chlorfentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide,tebufenozide; c) juvenoids: pyriproxyfen, methoprene (includingS-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors:spirodiclofen.

Other antiparasitics: acequinocyl, amitraz, AKD-1022, ANS-118,azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl,bromopropylate, BTG-504, BTG-505, camphechlor, cartap, chlorobenzilate,chlordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine,diacloden, diafenthiuron, DBI-3204, dinactin,dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan,ethiprole, ethofenprox, fenazaquin, flumite, MTI-800, fenpyroximate,fluacrypyrim, flubenzimine, flubrocythrinate, flufenzine, flufenprox,fluproxyfen, halofenprox, hydramethylnon, IKI-220, kanemite, NC-196,neem guard, nidinorterfuran, nitenpyram, SD-35651, WL-108477, pirydaryl,propargite, protrifenbute, pymethrozine, pyridaben, pyrimidifen,NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601,silafluofen, silomadine, spinosad, tebufenpyrad, tetradifon,tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad,triazamate, triethoxyspinosyn, trinactin, verbutin, vertalec, YI-5301.

Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki,Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenicbacteria, virus and fungi.

Bactericides: chlortetracycline, oxytetracycline, streptomycin.

Other biological agents: enrofloxacin, febantel, penethamate, moloxicam,cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin,benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin,tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel,triclabendazole.

The following mixtures of the compounds of formula (I) with activeingredients are preferred (the abbreviation “TX” means “one compoundselected from the group consisting of the compounds described in Tables1A to 30A, 1B to 29B, 1C to 33C, 1D to 27D or 1E to 27E (below), orTables T1a, T1b, T2a, T2b, T3a, T3b, T4a, T4b, T5a or T5b (below)”).

an adjuvant selected from the group of substances consisting ofpetroleum oils (alternative name) (628)+TX,

an acaricide selected from the group of substances consisting of1,1-bis(4-chlorophenyl)-2-ethoxyethanol (IUPAC name) (910)+TX,2,4-dichlorophenyl benzenesulfonate (IUPAC/Chemical Abstracts name)(1059)+TX, 2-fluoro-N-methyl-N-1-naphthylacetamide (IUPAC name)(1295)+TX, 4-chlorophenyl phenyl sulfone (IUPAC name) (981)+TX,abamectin (1)+TX, acequinocyl (3)+TX, acetoprole [CCN]+TX, acrinathrin(9)+TX, aldicarb (16)+TX, aldoxycarb (863)+TX, alpha-cypermethrin(202)+TX, amidithion (870)+TX, amidoflumet [CCN]+TX, amidothioate(872)+TX, amiton (875)+TX, amiton hydrogen oxalate (875)+TX, amitraz(24)+TX, aramite (881)+TX, arsenous oxide (882)+TX, AVI 382 (compoundcode)+TX, AZ 60541 (compound code)+TX, azinphos-ethyl (44)+TX,azinphos-methyl (45)+TX, azobenzene (IUPAC name) (888)+TX, azocyclotin(46)+TX, azothoate (889)+TX, benomyl (62)+TX, benoxafos (alternativename) [CCN]+TX, benzoximate (71)+TX, benzyl benzoate (IUPAC name)[CCN]+TX, bifenazate (74)+TX, bifenthrin (76)+TX, binapacryl (907)+TX,brofenvalerate (alternative name)+TX, bromocyclen (918)+TX, bromophos(920)+TX, bromophos-ethyl (921)+TX, bromopropylate (94)+TX, buprofezin(99)+TX, butocarboxim (103)+TX, butoxycarboxim (104)+TX, butylpyridaben(alternative name)+TX, calcium polysulfide (IUPAC name) (111)+TX,camphechlor (941)+TX, carbanolate (943)+TX, carbaryl (115)+TX,carbofuran (118)+TX, carbophenothion (947)+TX, CGA 50′439 (developmentcode) (125)+TX, chinomethionat (126)+TX, chlorbenside (959)+TX,chlordimeform (964)+TX, chlordimeform hydrochloride (964)+TX,chlorfenapyr (130)+TX, chlorfenethol (968)+TX, chlorfenson (970)+TX,chlorfensulfide (971)+TX, chlorfenvinphos (131)+TX, chlorobenzilate(975)+TX, chloromebuform (977)+TX, chloromethiuron (978)+TX,chloropropylate (983)+TX, chlorpyrifos (145)+TX, chlorpyrifos-methyl(146)+TX, chlorthiophos (994)+TX, cinerin 1 (696)+TX, cinerin II(696)+TX, cinerins (696)+TX, clofentezine (158)+TX, closantel(alternative name) [CCN]+TX, coumaphos (174)+TX, crotamiton (alternativename) [CCN]+TX, crotoxyphos (1010)+TX, cufraneb (1013)+TX, cyanthoate(1020)+TX, cyflumetofen (CAS Reg. No.: 400882-07-7)+TX, cyhalothrin(196)+TX, cyhexatin (199)+TX, cypermethrin (201)+TX, DCPM (1032)+TX, DDT(219)+TX, demephion (1037)+TX, demephion-O (1037)+TX, demephion-S(1037)+TX, demeton (1038)+TX, demeton-methyl (224)+TX, demeton-O(1038)+TX, demeton-O-methyl (224)+TX, demeton-S (1038)+TX,demeton-S-methyl (224)+TX, demeton-S-methylsulfon (1039)+TX,diafenthiuron (226)+TX, dialifos (1042)+TX, diazinon (227)+TX,dichlofluanid (230)+TX, dichlorvos (236)+TX, dicliphos (alternativename)+TX, dicofol (242)+TX, dicrotophos (243)+TX, dienochlor (1071)+TX,dimefox (1081)+TX, dimethoate (262)+TX, dinactin (alternative name)(653)+TX, dinex (1089)+TX, dinex-diclexine (1089)+TX, dinobuton(269)+TX, dinocap (270)+TX, dinocap-4 [CCN]+TX, dinocap-6 [CCN]+TX,dinocton (1090)+TX, dinopenton (1092)+TX, dinosulfon (1097)+TX,dinoterbon (1098)+TX, dioxathion (1102)+TX, diphenyl sulfone (IUPACname) (1103)+TX, disulfiram (alternative name) [CCN]+TX, disulfoton(278)+TX, DNOC (282)+TX, dofenapyn (1113)+TX, doramectin (alternativename) [CCN]+TX, endosulfan (294)+TX, endothion (1121)+TX, EPN (297)+TX,eprinomectin (alternative name) [CCN]+TX, ethion (309)+TX,ethoate-methyl (1134)+TX, etoxazole (320)+TX, etrimfos (1142)+TX,fenazaflor (1147)+TX, fenazaquin (328)+TX, fenbutatin oxide (330)+TX,fenothiocarb (337)+TX, fenpropathrin (342)+TX, fenpyrad (alternativename)+TX, fenpyroximate (345)+TX, fenson (1157)+TX, fentrifanil(1161)+TX, fenvalerate (349)+TX, fipronil (354)+TX, fluacrypyrim(360)+TX, fluazuron (1166)+TX, flubenzimine (1167)+TX, flucycloxuron(366)+TX, flucythrinate (367)+TX, fluenetil (1169)+TX, flufenoxuron(370)+TX, flumethrin (372)+TX, fluorbenside (1174)+TX, fluvalinate(1184)+TX, FMC 1137 (development code) (1185)+TX, formetanate (405)+TX,formetanate hydrochloride (405)+TX, formothion (1192)+TX, formparanate(1193)+TX, gamma-HCH (430)+TX, glyodin (1205)+TX, halfenprox (424)+TX,heptenophos (432)+TX, hexadecyl cyclopropanecarboxylate (IUPAC/ChemicalAbstracts name) (1216)+TX, hexythiazox (441)+TX, iodomethane (IUPACname) (542)+TX, isocarbophos (alternative name) (473)+TX, isopropylO-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473)+TX,ivermectin (alternative name) [CCN]+TX, jasmolin I (696)+TX, jasmolin II(696)+TX, jodfenphos (1248)+TX, lindane (430)+TX, lufenuron (490)+TX,malathion (492)+TX, malonoben (1254)+TX, mecarbam (502)+TX, mephosfolan(1261)+TX, mesulfen (alternative name) [CCN]+TX, methacrifos (1266)+TX,methamidophos (527)+TX, methidathion (529)+TX, methiocarb (530)+TX,methomyl (531)+TX, methyl bromide (537)+TX, metolcarb (550)+TX,mevinphos (556)+TX, mexacarbate (1290)+TX, milbemectin (557)+TX,milbemycin oxime (alternative name) [CCN]+TX, mipafox (1293)+TX,monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin (alternativename) [CCN]+TX, naled (567)+TX, NC-184 (compound code)+TX, NC-512(compound code)+TX, nifluridide (1309)+TX, nikkomycins (alternativename) [CCN]+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1 zinc chloridecomplex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250 (compoundcode)+TX, omethoate (594)+TX, oxamyl (602)+TX, oxydeprofos (1324)+TX,oxydisulfoton (1325)+TX, pp′-DDT (219)+TX, parathion (615)+TX,permethrin (626)+TX, petroleum oils (alternative name) (628)+TX,phenkapton (1330)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone(637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosphamidon (639)+TX,phoxim (642)+TX, pirimiphos-methyl (652)+TX, polychloroterpenes(traditional name) (1347)+TX, polynactins (alternative name) (653)+TX,proclonol (1350)+TX, profenofos (662)+TX, promacyl (1354)+TX, propargite(671)+TX, propetamphos (673)+TX, propoxur (678)+TX, prothidathion(1360)+TX, prothoate (1362)+TX, pyrethrin I (696)+TX, pyrethrin II(696)+TX, pyrethrins (696)+TX, pyridaben (699)+TX, pyridaphenthion(701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, quinalphos(711)+TX, quintiofos (1381)+TX, R-1492 (development code) (1382)+TX,RA-17 (development code) (1383)+TX, rotenone (722)+TX, schradan(1389)+TX, sebufos (alternative name)+TX, selamectin (alternative name)[CCN]+TX, SI-0009 (compound code)+TX, sophamide (1402)+TX, spirodiclofen(738)+TX, spiromesifen (739)+TX, SSI-121 (development code) (1404)+TX,sulfiram (alternative name) [CCN]+TX, sulfluramid (750)+TX, sulfotep(753)+TX, sulfur (754)+TX, SZI-121 (development code) (757)+TX,tau-fluvalinate (398)+TX, tebufenpyrad (763)+TX, TEPP (1417)+TX, terbam(alternative name)+TX, tetrachlorvinphos (777)+TX, tetradifon (786)+TX,tetranactin (alternative name) (653)+TX, tetrasul (1425)+TX, thiafenox(alternative name)+TX, thiocarboxime (1431)+TX, thiofanox (800)+TX,thiometon (801)+TX, thioquinox (1436)+TX, thuringiensin (alternativename) [CCN]+TX, triamiphos (1441)+TX, triarathene (1443)+TX, triazophos(820)+TX, triazuron (alternative name)+TX, trichlorfon (824)+TX,trifenofos (1455)+TX, trinactin (alternative name) (653)+TX, vamidothion(847)+TX, vaniliprole [CCN] and YI-5302 (compound code)+TX,

an algicide selected from the group of substances consisting ofbethoxazin [CCN]+TX, copper dioctanoate (IUPAC name) (170)+TX, coppersulfate (172)+TX, cybutryne [CCN]+TX, dichlone (1052)+TX, dichlorophen(232)+TX, endothal (295)+TX, fentin (347)+TX, hydrated lime [CCN]+TX,nabam (566)+TX, quinoclamine (714)+TX, quinonamid (1379)+TX, simazine(730)+TX, triphenyltin acetate (IUPAC name) (347) and triphenyltinhydroxide (IUPAC name) (347)+TX,

an anthelmintic selected from the group of substances consisting ofabamectin (1)+TX, crufomate (1011)+TX, doramectin (alternative name)[CCN]+TX, emamectin (291)+TX, emamectin benzoate (291)+TX, eprinomectin(alternative name) [CCN]+TX, ivermectin (alternative name) [CCN]+TX,milbemycin oxime (alternative name) [CCN]+TX, moxidectin (alternativename) [CCN]+TX, piperazine [CCN]+TX, selamectin (alternative name)[CCN]+TX, spinosad (737) and thiophanate (1435)+TX,

an avicide selected from the group of substances consisting ofchloralose (127)+TX, endrin (1122)+TX, fenthion (346)+TX,pyridin-4-amine (IUPAC name) (23) and strychnine (745)+TX,

a bactericide selected from the group of substances consisting of1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222)+TX,4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748)+TX,8-hydroxyquinoline sulfate (446)+TX, bronopol (97)+TX, copperdioctanoate (IUPAC name) (170)+TX, copper hydroxide (IUPAC name)(169)+TX, cresol [CCN]+TX, dichlorophen (232)+TX, dipyrithione(1105)+TX, dodicin (1112)+TX, fenaminosulf (1144)+TX, formaldehyde(404)+TX, hydrargaphen (alternative name) [CCN]+TX, kasugamycin(483)+TX, kasugamycin hydrochloride hydrate (483)+TX, nickelbis(dimethyldithiocarbamate) (IUPAC name) (1308)+TX, nitrapyrin(580)+TX, octhilinone (590)+TX, oxolinic acid (606)+TX, oxytetracycline(611)+TX, potassium hydroxyquinoline sulfate (446)+TX, probenazole(658)+TX, streptomycin (744)+TX, streptomycin sesquisulfate (744)+TX,tecloftalam (766)+TX, and thiomersal (alternative name) [CCN]+TX,

a biological agent selected from the group of substances consisting ofAdoxophyes orana GV (alternative name) (12)+TX, Agrobacteriumradiobacter (alternative name) (13)+TX, Amblyseius spp. (alternativename) (19)+TX, Anagrapha falcifera NPV (alternative name) (28)+TX,Anagrus atomus (alternative name) (29)+TX, Aphelinus abdominalis(alternative name) (33)+TX, Aphidius colemani (alternative name)(34)+TX, Aphidoletes aphidimyza (alternative name) (35)+TX, Autographacalifornica NPV (alternative name) (38)+TX, Bacillus firmus (alternativename) (48)+TX, Bacillus sphaericus Neide (scientific name) (49)+TX,Bacillus thuringiensis Berliner (scientific name) (51)+TX, Bacillusthuringiensis subsp. aizawai (scientific name) (51)+TX, Bacillusthuringiensis subsp. israelensis (scientific name) (51)+TX, Bacillusthuringiensis subsp. japonensis (scientific name) (51)+TX, Bacillusthuringiensis subsp. kurstaki (scientific name) (51)+TX, Bacillusthuringiensis subsp. tenebrionis (scientific name) (51)+TX, Beauveriabassiana (alternative name) (53)+TX, Beauveria brongniartii (alternativename) (54)+TX, Chrysoperla carnea (alternative name) (151)+TX,Cryptolaemus montrouzieri (alternative name) (178)+TX, Cydia pomonellaGV (alternative name) (191)+TX, Dacnusa sibirica (alternative name)(212)+TX, Diglyphus isaea (alternative name) (254)+TX, Encarsia formosa(scientific name) (293)+TX, Eretmocerus eremicus (alternative name)(300)+TX, Helicoverpa zea NPV (alternative name) (431)+TX,Heterorhabditis bacteriophora and H. megidis (alternative name)(433)+TX, Hippodamia convergens (alternative name) (442)+TX, Leptomastixdactylopii (alternative name) (488)+TX, Macrolophus caliginosus(alternative name) (491)+TX, Mamestra brassicae NPV (alternative name)(494)+TX, Metaphycus helvolus (alternative name) (522)+TX, Metarhiziumanisopliae var. acridum (scientific name) (523)+TX, Metarhiziumanisopliae var. anisopliae (scientific name) (523)+TX, Neodiprionsertifer NPV and N. lecontei NPV (alternative name) (575)+TX, Orius spp.(alternative name) (596)+TX, Paecilomyces fumosoroseus (alternativename) (613)+TX, Phytoseiulus persimilis (alternative name) (644)+TX,Spodoptera exigua multicapsid nuclear polyhedrosis virus (scientificname) (741)+TX, Steinernema bibionis (alternative name) (742)+TX,Steinernema carpocapsae (alternative name) (742)+TX, Steinernema feltiae(alternative name) (742)+TX, Steinernema glaseri (alternative name)(742)+TX, Steinernema riobrave (alternative name) (742)+TX, Steinernemariobravis (alternative name) (742)+TX, Steinernema scapterisci(alternative name) (742)+TX, Steinernema spp. (alternative name)(742)+TX, Trichogramma spp. (alternative name) (826)+TX, Typhlodromusoccidentalis (alternative name) (844) and Verticillium lecanii(alternative name) (848)+TX,

a soil sterilant selected from the group of substances consisting ofiodomethane (IUPAC name) (542) and methyl bromide (537)+TX,

a chemosterilant selected from the group of substances consisting ofapholate [CCN]+TX, bisazir (alternative name) [CCN]+TX, busulfan(alternative name) [CCN]+TX, diflubenzuron (250)+TX, dimatif(alternative name) [CCN]+TX, hemel [CCN]+TX, hempa [CCN]+TX, metepa[CCN]+TX, methiotepa [CCN]+TX, methyl apholate [CCN]+TX, morzid[CCN]+TX, penfluron (alternative name) [CCN]+TX, tepa [CCN]+TX,thiohempa (alternative name) [CCN]+TX, thiotepa (alternative name)[CCN]+TX, tretamine (alternative name) [CCN] and uredepa (alternativename) [CCN]+TX,

an insect pheromone selected from the group of substances consisting of(E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol (IUPAC name) (222)+TX,(E)-tridec-4-en-1-yl acetate (IUPAC name) (829)+TX,(E)-6-methylhept-2-en-4-ol (IUPAC name) (541)+TX,(E,Z)-tetradeca-4,10-dien-1-yl acetate (IUPAC name) (779)+TX,(Z)-dodec-7-en-1-yl acetate (IUPAC name) (285)+TX, (Z)-hexadec-11-enal(IUPAC name) (436)+TX, (Z)-hexadec-11-en-1-yl acetate (IUPAC name)(437)+TX, (Z)-hexadec-13-en-11-yn-1-yl acetate (IUPAC name) (438)+TX,(Z)-icos-13-en-10-one (IUPAC name) (448)+TX, (Z)-tetradec-7-en-1-al(IUPAC name) (782)+TX, (Z)-tetradec-9-en-1-ol (IUPAC name) (783)+TX,(Z)-tetradec-9-en-1-yl acetate (IUPAC name) (784)+TX,(7E,9Z)-dodeca-7,9-dien-1-yl acetate (IUPAC name) (283)+TX,(9Z,11E)-tetradeca-9,11-dien-1-yl acetate (IUPAC name) (780)+TX,(9Z,12E)-tetradeca-9,12-dien-1-yl acetate (IUPAC name) (781)+TX,14-methyloctadec-1-ene (IUPAC name) (545)+TX, 4-methylnonan-5-ol with4-methylnonan-5-one (IUPAC name) (544)+TX, alpha-multistriatin(alternative name) [CCN]+TX, brevicomin (alternative name) [CCN]+TX,codlelure (alternative name) [CCN]+TX, codlemone (alternative name)(167)+TX, cuelure (alternative name) (179)+TX, disparlure (277)+TX,dodec-8-en-1-yl acetate (IUPAC name) (286)+TX, dodec-9-en-1-yl acetate(IUPAC name) (287)+TX, dodeca-8+TX, 10-dien-1-yl acetate (IUPAC name)(284)+TX, dominicalure (alternative name) [CCN]+TX, ethyl4-methyloctanoate (IUPAC name) (317)+TX, eugenol (alternative name)[CCN]+TX, frontalin (alternative name) [CCN]+TX, gossyplure (alternativename) (420)+TX, grandlure (421)+TX, grandlure I (alternative name)(421)+TX, grandlure II (alternative name) (421)+TX, grandlure III(alternative name) (421)+TX, grandlure IV (alternative name) (421)+TX,hexalure [CCN]+TX, ipsdienol (alternative name) [CCN]+TX, ipsenol(alternative name) [CCN]+TX, japonilure (alternative name) (481)+TX,lineatin (alternative name) [CCN]+TX, litlure (alternative name)[CCN]+TX, looplure (alternative name) [CCN]+TX, medlure [CCN]+TX,megatomoic acid (alternative name) [CCN]+TX, methyl eugenol (alternativename) (540)+TX, muscalure (563)+TX, octadeca-2,13-dien-1-yl acetate(IUPAC name) (588)+TX, octadeca-3,13-dien-1-yl acetate (IUPAC name)(589)+TX, orfralure (alternative name) [CCN]+TX, oryctalure (alternativename) (317)+TX, ostramone (alternative name) [CCN]+TX, siglure [CCN]+TX,sordidin (alternative name) (736)+TX, sulcatol (alternative name)[CCN]+TX, tetradec-11-en-1-yl acetate (IUPAC name) (785)+TX, trimedlure(839)+TX, trimedlure A (alternative name) (839)+TX, trimedlure B₁(alternative name) (839)+TX, trimedlure B₂ (alternative name) (839)+TX,trimedlure C (alternative name) (839) and trunc-call (alternative name)[CCN]+TX,

an insect repellent selected from the group of substances consisting of2-(octylthio)ethanol (IUPAC name) (591)+TX, butopyronoxyl (933)+TX,butoxy(polypropylene glycol) (936)+TX, dibutyl adipate (IUPAC name)(1046)+TX, dibutyl phthalate (1047)+TX, dibutyl succinate (IUPAC name)(1048)+TX, diethyltoluamide [CCN]+TX, dimethyl carbate [CCN]+TX,dimethyl phthalate [CCN]+TX, ethyl hexanediol (1137)+TX, hexamide[CCN]+TX, methoquin-butyl (1276)+TX, methylneodecanamide [CCN]+TX,oxamate [CCN] and picaridin [CCN]+TX,

an insecticide selected from the group of substances consisting of1-dichloro-1-nitroethane (IUPAC/Chemical Abstracts name) (1058)+TX,1,1-dichloro-2,2-bis(4-ethylphenyl)ethane (IUPAC name) (1056), +TX,1,2-dichloropropane (IUPAC/Chemical Abstracts name) (1062)+TX,1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063)+TX,1-bromo-2-chloroethane (IUPAC/Chemical Abstracts name) (916)+TX,2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate (IUPAC name)(1451)+TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate(IUPAC name) (1066)+TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate(IUPAC/Chemical Abstracts name) (1109)+TX, 2-(2-butoxyethoxy)ethylthiocyanate (IUPAC/Chemical Abstracts name) (935)+TX,2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate (IUPAC/ChemicalAbstracts name) (1084)+TX, 2-(4-chloro-3,5-xylyloxy)ethanol (IUPAC name)(986)+TX, 2-chlorovinyl diethyl phosphate (IUPAC name) (984)+TX,2-imidazolidone (IUPAC name) (1225)+TX, 2-isovalerylindan-1,3-dione(IUPAC name) (1246)+TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate(IUPAC name) (1284)+TX, 2-thiocyanatoethyl laurate (IUPAC name)(1433)+TX, 3-bromo-1-chloroprop-1-ene (IUPAC name) (917)+TX,3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate (IUPAC name) (1283)+TX,4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate (IUPAC name)(1285)+TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate (IUPACname) (1085)+TX, abamectin (1)+TX, acephate (2)+TX, acetamiprid (4)+TX,acethion (alternative name) [CCN]+TX, acetoprole [CCN]+TX, acrinathrin(9)+TX, acrylonitrile (IUPAC name) (861)+TX, alanycarb (15)+TX, aldicarb(16)+TX, aldoxycarb (863)+TX, aldrin (864)+TX, allethrin (17)+TX,allosamidin (alternative name) [CCN]+TX, allyxycarb (866)+TX,alpha-cypermethrin (202)+TX, alpha-ecdysone (alternative name) [CCN]+TX,aluminium phosphide (640)+TX, amidithion (870)+TX, amidothioate(872)+TX, aminocarb (873)+TX, amiton (875)+TX, amiton hydrogen oxalate(875)+TX, amitraz (24)+TX, anabasine (877)+TX, athidathion (883)+TX, AVI382 (compound code)+TX, AZ 60541 (compound code)+TX, azadirachtin(alternative name) (41)+TX, azamethiphos (42)+TX, azinphos-ethyl(44)+TX, azinphos-methyl (45)+TX, azothoate (889)+TX, Bacillusthuringiensis delta endotoxins (alternative name) (52)+TX, bariumhexafluorosilicate (alternative name) [CCN]+TX, barium polysulfide(IUPAC/Chemical Abstracts name) (892)+TX, barthrin [CCN]+TX, Bayer22/190 (development code) (893)+TX, Bayer 22408 (development code)(894)+TX, bendiocarb (58)+TX, benfuracarb (60)+TX, bensultap (66)+TX,benzovindiflupyr+TX, beta-cyfluthrin (194)+TX, beta-cypermethrin(203)+TX, bifenthrin (76)+TX, bioallethrin (78)+TX, bioallethrinS-cyclopentenyl isomer (alternative name) (79)+TX, bioethanomethrin[CCN]+TX, biopermethrin (908)+TX, bioresmethrin (80)+TX,bis(2-chloroethyl) ether (IUPAC name) (909)+TX, bistrifluron (83)+TX,borax (86)+TX, brofenvalerate (alternative name)+TX, bromfenvinfos(914)+TX, bromocyclen (918)+TX, bromo-DDT (alternative name) [CCN]+TX,bromophos (920)+TX, bromophos-ethyl (921)+TX, bufencarb (924)+TX,buprofezin (99)+TX, butacarb (926)+TX, butathiofos (927)+TX,butocarboxim (103)+TX, butonate (932)+TX, butoxycarboxim (104)+TX,butylpyridaben (alternative name)+TX, cadusafos (109)+TX, calciumarsenate [CCN]+TX, calcium cyanide (444)+TX, calcium polysulfide (IUPACname) (111)+TX, camphechlor (941)+TX, carbanolate (943)+TX, carbaryl(115)+TX, carbofuran (118)+TX, carbon disulfide (IUPAC/ChemicalAbstracts name) (945)+TX, carbon tetrachloride (IUPAC name) (946)+TX,carbophenothion (947)+TX, carbosulfan (119)+TX, cartap (123)+TX, cartaphydrochloride (123)+TX, cevadine (alternative name) (725)+TX,chlorbicyclen (960)+TX, chlordane (128)+TX, chlordecone (963)+TX,chlordimeform (964)+TX, chlordimeform hydrochloride (964)+TX,chlorethoxyfos (129)+TX, chlorfenapyr (130)+TX, chlorfenvinphos(131)+TX, chlorfluazuron (132)+TX, chlormephos (136)+TX, chloroform[CCN]+TX, chloropicrin (141)+TX, chlorphoxim (989)+TX, chlorprazophos(990)+TX, chlorpyrifos (145)+TX, chlorpyrifos-methyl (146)+TX,chlorthiophos (994)+TX, chromafenozide (150)+TX, cinerin 1 (696)+TX,cinerin II (696)+TX, cinerins (696)+TX, cis-resmethrin (alternativename)+TX, cismethrin (80)+TX, clocythrin (alternative name)+TX,cloethocarb (999)+TX, closantel (alternative name) [CCN]+TX,clothianidin (165)+TX, copper acetoarsenite [CCN]+TX, copper arsenate[CCN]+TX, copper oleate [CCN]+TX, coumaphos (174)+TX, coumithoate(1006)+TX, crotamiton (alternative name) [CCN]+TX, crotoxyphos(1010)+TX, crufomate (1011)+TX, cryolite (alternative name) (177)+TX, CS708 (development code) (1012)+TX, cyanofenphos (1019)+TX, cyanophos(184)+TX, cyanthoate (1020)+TX, cyclethrin [CCN]+TX, cycloprothrin(188)+TX, cyfluthrin (193)+TX, cyhalothrin (196)+TX, cypermethrin(201)+TX, cyphenothrin (206)+TX, cyromazine (209)+TX, cythioate(alternative name) [CCN]+TX, d-limonene (alternative name) [CCN]+TX,d-tetramethrin (alternative name) (788)+TX, DAEP (1031)+TX, dazomet(216)+TX, DDT (219)+TX, decarbofuran (1034)+TX, deltamethrin (223)+TX,demephion (1037)+TX, demephion-O (1037)+TX, demephion-S (1037)+TX,demeton (1038)+TX, demeton-methyl (224)+TX, demeton-O (1038)+TX,demeton-O-methyl (224)+TX, demeton-S (1038)+TX, demeton-S-methyl(224)+TX, demeton-S-methylsulphon (1039)+TX, diafenthiuron (226)+TX,dialifos (1042)+TX, diamidafos (1044)+TX, diazinon (227)+TX, dicapthon(1050)+TX, dichlofenthion (1051)+TX, dichlorvos (236)+TX, dicliphos(alternative name)+TX, dicresyl (alternative name) [CCN]+TX, dicrotophos(243)+TX, dicyclanil (244)+TX, dieldrin (1070)+TX, diethyl5-methylpyrazol-3-yl phosphate (IUPAC name) (1076)+TX, diflubenzuron(250)+TX, dilor (alternative name) [CCN]+TX, dimefluthrin [CCN]+TX,dimefox (1081)+TX, dimetan (1085)+TX, dimethoate (262)+TX, dimethrin(1083)+TX, dimethylvinphos (265)+TX, dimetilan (1086)+TX, dinex(1089)+TX, dinex-diclexine (1089)+TX, dinoprop (1093)+TX, dinosam(1094)+TX, dinoseb (1095)+TX, dinotefuran (271)+TX, diofenolan(1099)+TX, dioxabenzofos (1100)+TX, dioxacarb (1101)+TX, dioxathion(1102)+TX, disulfoton (278)+TX, dithicrofos (1108)+TX, DNOC (282)+TX,doramectin (alternative name) [CCN]+TX, DSP (1115)+TX, ecdysterone(alternative name) [CCN]+TX, EI 1642 (development code) (1118)+TX,emamectin (291)+TX, emamectin benzoate (291)+TX, EMPC (1120)+TX,empenthrin (292)+TX, endosulfan (294)+TX, endothion (1121)+TX, endrin(1122)+TX, EPBP (1123)+TX, EPN (297)+TX, epofenonane (1124)+TX,eprinomectin (alternative name) [CCN]+TX, esfenvalerate (302)+TX,etaphos (alternative name) [CCN]+TX, ethiofencarb (308)+TX, ethion(309)+TX, ethiprole (310)+TX, ethoate-methyl (1134)+TX, ethoprophos(312)+TX, ethyl formate (IUPAC name) [CCN]+TX, ethyl-DDD (alternativename) (1056)+TX, ethylene dibromide (316)+TX, ethylene dichloride(chemical name) (1136)+TX, ethylene oxide [CCN]+TX, etofenprox (319)+TX,etrimfos (1142)+TX, EXD (1143)+TX, famphur (323)+TX, fenamiphos(326)+TX, fenazaflor (1147)+TX, fenchlorphos (1148)+TX, fenethacarb(1149)+TX, fenfluthrin (1150)+TX, fenitrothion (335)+TX, fenobucarb(336)+TX, fenoxacrim (1153)+TX, fenoxycarb (340)+TX, fenpirithrin(1155)+TX, fenpropathrin (342)+TX, fenpyrad (alternative name)+TX,fensulfothion (1158)+TX, fenthion (346)+TX, fenthion-ethyl [CCN]+TX,fenvalerate (349)+TX, fipronil (354)+TX, flonicamid (358)+TX,flubendiamide (CAS. Reg. No.: 272451-65-7)+TX, flucofuron (1168)+TX,flucycloxuron (366)+TX, flucythrinate (367)+TX, fluenetil (1169)+TX,flufenerim [CCN]+TX, flufenoxuron (370)+TX, flufenprox (1171)+TX,flumethrin (372)+TX, fluvalinate (1184)+TX, FMC 1137 (development code)(1185)+TX, fonofos (1191)+TX, formetanate (405)+TX, formetanatehydrochloride (405)+TX, formothion (1192)+TX, formparanate (1193)+TX,fosmethilan (1194)+TX, fospirate (1195)+TX, fosthiazate (408)+TX,fosthietan (1196)+TX, furathiocarb (412)+TX, furethrin (1200)+TX,gamma-cyhalothrin (197)+TX, gamma-HCH (430)+TX, guazatine (422)+TX,guazatine acetates (422)+TX, GY-81 (development code) (423)+TX,halfenprox (424)+TX, halofenozide (425)+TX, HCH (430)+TX, HEOD(1070)+TX, heptachlor (1211)+TX, heptenophos (432)+TX, heterophos[CCN]+TX, hexaflumuron (439)+TX, HHDN (864)+TX, hydramethylnon (443)+TX,hydrogen cyanide (444)+TX, hydroprene (445)+TX, hyquincarb (1223)+TX,imidacloprid (458)+TX, imiprothrin (460)+TX, indoxacarb (465)+TX,iodomethane (IUPAC name) (542)+TX, IPSP (1229)+TX, isazofos (1231)+TX,isobenzan (1232)+TX, isocarbophos (alternative name) (473)+TX, isodrin(1235)+TX, isofenphos (1236)+TX, isolane (1237)+TX, isoprocarb (472)+TX,isopropyl O-(methoxyaminothiophosphoryl)salicylate (IUPAC name)(473)+TX, isoprothiolane (474)+TX, isothioate (1244)+TX, isoxathion(480)+TX, ivermectin (alternative name) [CCN]+TX, jasmolin I (696)+TX,jasmolin II (696)+TX, jodfenphos (1248)+TX, juvenile hormone I(alternative name) [CCN]+TX, juvenile hormone II (alternative name)[CCN]+TX, juvenile hormone Ill (alternative name) [CCN]+TX, kelevan(1249)+TX, kinoprene (484)+TX, lambda-cyhalothrin (198)+TX, leadarsenate [CCN]+TX, lepimectin (CCN)+TX, leptophos (1250)+TX, lindane(430)+TX, lirimfos (1251)+TX, lufenuron (490)+TX, lythidathion(1253)+TX, m-cumenyl methylcarbamate (IUPAC name) (1014)+TX, magnesiumphosphide (IUPAC name) (640)+TX, malathion (492)+TX, malonoben(1254)+TX, mazidox (1255)+TX, mecarbam (502)+TX, mecarphon (1258)+TX,menazon (1260)+TX, mephosfolan (1261)+TX, mercurous chloride (513)+TX,mesulfenfos (1263)+TX, metaflumizone (CCN)+TX, metam (519)+TX,metam-potassium (alternative name) (519)+TX, metam-sodium (519)+TX,methacrifos (1266)+TX, methamidophos (527)+TX, methanesulfonyl fluoride(IUPAC/Chemical Abstracts name) (1268)+TX, methidathion (529)+TX,methiocarb (530)+TX, methocrotophos (1273)+TX, methomyl (531)+TX,methoprene (532)+TX, methoquin-butyl (1276)+TX, methothrin (alternativename) (533)+TX, methoxychlor (534)+TX, methoxyfenozide (535)+TX, methylbromide (537)+TX, methyl isothiocyanate (543)+TX, methylchloroform(alternative name) [CCN]+TX, methylene chloride [CCN]+TX, metofluthrin[CCN]+TX, metolcarb (550)+TX, metoxadiazone (1288)+TX, mevinphos(556)+TX, mexacarbate (1290)+TX, milbemectin (557)+TX, milbemycin oxime(alternative name) [CCN]+TX, mipafox (1293)+TX, mirex (1294)+TX,monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin (alternativename) [CCN]+TX, naftalofos (alternative name) [CCN]+TX, naled (567)+TX,naphthalene (IUPAC/Chemical Abstracts name) (1303)+TX, NC-170(development code) (1306)+TX, NC-184 (compound code)+TX, nicotine(578)+TX, nicotine sulfate (578)+TX, nifluridide (1309)+TX, nitenpyram(579)+TX, nithiazine (1311)+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1zinc chloride complex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250(compound code)+TX, nornicotine (traditional name) (1319)+TX, novaluron(585)+TX, noviflumuron (586)+TX, 0-5-dichloro-4-iodophenyl O-ethylethylphosphonothioate (IUPAC name) (1057)+TX, O,O-diethylO-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate (IUPAC name)(1074)+TX, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-ylphosphorothioate (IUPAC name) (1075)+TX, O,O,O′,O′-tetrapropyldithiopyrophosphate (IUPAC name) (1424)+TX, oleic acid (IUPAC name)(593)+TX, omethoate (594)+TX, oxamyl (602)+TX, oxydemeton-methyl(609)+TX, oxydeprofos (1324)+TX, oxydisulfoton (1325)+TX, pp′-DDT(219)+TX, para-dichlorobenzene [CCN]+TX, parathion (615)+TX,parathion-methyl (616)+TX, penfluron (alternative name) [CCN]+TX,pentachlorophenol (623)+TX, pentachlorophenyl laurate (IUPAC name)(623)+TX, permethrin (626)+TX, petroleum oils (alternative name)(628)+TX, PH 60-38 (development code) (1328)+TX, phenkapton (1330)+TX,phenothrin (630)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone(637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosnichlor (1339)+TX,phosphamidon (639)+TX, phosphine (IUPAC name) (640)+TX, phoxim (642)+TX,phoxim-methyl (1340)+TX, pirimetaphos (1344)+TX, pirimicarb (651)+TX,pirimiphos-ethyl (1345)+TX, pirimiphos-methyl (652)+TX,polychlorodicyclopentadiene isomers (IUPAC name) (1346)+TX,polychloroterpenes (traditional name) (1347)+TX, potassium arsenite[CCN]+TX, potassium thiocyanate [CCN]+TX, prallethrin (655)+TX,precocene I (alternative name) [CCN]+TX, precocene II (alternative name)[CCN]+TX, precocene III (alternative name) [CCN]+TX, primidophos(1349)+TX, profenofos (662)+TX, profluthrin [CCN]+TX, promacyl(1354)+TX, promecarb (1355)+TX, propaphos (1356)+TX, propetamphos(673)+TX, propoxur (678)+TX, prothidathion (1360)+TX, prothiofos(686)+TX, prothoate (1362)+TX, protrifenbute [CCN]+TX, pymetrozine(688)+TX, pyraclofos (689)+TX, pyrazophos (693)+TX, pyresmethrin(1367)+TX, pyrethrin I (696)+TX, pyrethrin II (696)+TX, pyrethrins(696)+TX, pyridaben (699)+TX, pyridalyl (700)+TX, pyridaphenthion(701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, pyriproxyfen(708)+TX, quassia (alternative name) [CCN]+TX, quinalphos (711)+TX,quinalphos-methyl (1376)+TX, quinothion (1380)+TX, quintiofos (1381)+TX,R-1492 (development code) (1382)+TX, rafoxanide (alternative name)[CCN]+TX, resmethrin (719)+TX, rotenone (722)+TX, RU 15525 (developmentcode) (723)+TX, RU 25475 (development code) (1386)+TX, ryania(alternative name) (1387)+TX, ryanodine (traditional name) (1387)+TX,sabadilla (alternative name) (725)+TX, schradan (1389)+TX, sebufos(alternative name)+TX, selamectin (alternative name) [CCN]+TX, SI-0009(compound code)+TX, SI-0205 (compound code)+TX, SI-0404 (compoundcode)+TX, SI-0405 (compound code)+TX, silafluofen (728)+TX, SN 72129(development code) (1397)+TX, sodium arsenite [CCN]+TX, sodium cyanide(444)+TX, sodium fluoride (IUPAC/Chemical Abstracts name) (1399)+TX,sodium hexafluorosilicate (1400)+TX, sodium pentachlorophenoxide(623)+TX, sodium selenate (IUPAC name) (1401)+TX, sodium thiocyanate[CCN]+TX, sophamide (1402)+TX, spinosad (737)+TX, spiromesifen (739)+TX,spirotetrmat (CCN)+TX, sulcofuron (746)+TX, sulcofuron-sodium (746)+TX,sulfluramid (750)+TX, sulfotep (753)+TX, sulfuryl fluoride (756)+TX,sulprofos (1408)+TX, tar oils (alternative name) (758)+TX,tau-fluvalinate (398)+TX, tazimcarb (1412)+TX, TDE (1414)+TX,tebufenozide (762)+TX, tebufenpyrad (763)+TX, tebupirimfos (764)+TX,teflubenzuron (768)+TX, tefluthrin (769)+TX, temephos (770)+TX, TEPP(1417)+TX, terallethrin (1418)+TX, terbam (alternative name)+TX,terbufos (773)+TX, tetrachloroethane [CCN]+TX, tetrachlorvinphos(777)+TX, tetramethrin (787)+TX, theta-cypermethrin (204)+TX,thiacloprid (791)+TX, thiafenox (alternative name)+TX, thiamethoxam(792)+TX, thicrofos (1428)+TX, thiocarboxime (1431)+TX, thiocyclam(798)+TX, thiocyclam hydrogen oxalate (798)+TX, thiodicarb (799)+TX,thiofanox (800)+TX, thiometon (801)+TX, thionazin (1434)+TX, thiosultap(803)+TX, thiosultap-sodium (803)+TX, thuringiensin (alternative name)[CCN]+TX, tolfenpyrad (809)+TX, tralomethrin (812)+TX, transfluthrin(813)+TX, transpermethrin (1440)+TX, triamiphos (1441)+TX, triazamate(818)+TX, triazophos (820)+TX, triazuron (alternative name)+TX,trichlorfon (824)+TX, trichlormetaphos-3 (alternative name) [CCN]+TX,trichloronat (1452)+TX, trifenofos (1455)+TX, triflumuron (835)+TX,trimethacarb (840)+TX, triprene (1459)+TX, vamidothion (847)+TX,vaniliprole [CCN]+TX, veratridine (alternative name) (725)+TX, veratrine(alternative name) (725)+TX, XMC (853)+TX, xylylcarb (854)+TX, YI-5302(compound code)+TX, zeta-cypermethrin (205)+TX, zetamethrin (alternativename)+TX, zinc phosphide (640)+TX, zolaprofos (1469) and ZXI 8901(development code) (858)+TX, cyantraniliprole [736994-63-19+TX,chlorantraniliprole [500008-45-7]+TX, cyenopyrafen [560121-52-0]+TX,cyflumetofen [400882-07-7]+TX, pyrifluquinazon [337458-27-2]+TX,spinetoram [187166-40-1+187166-15-0]+TX, spirotetramat [203313-25-1]+TX,sulfoxaflor [946578-00-3]+TX, flufiprole [704886-18-0]+TX, meperfluthrin[915288-13-0]+TX, tetramethylfluthrin [84937-88-2]+TX, triflumezopyrim(disclosed in WO 2012/092115)+TX,

a molluscicide selected from the group of substances consisting ofbis(tributyltin) oxide (IUPAC name) (913)+TX, bromoacetamide [CCN]+TX,calcium arsenate [CCN]+TX, cloethocarb (999)+TX, copper acetoarsenite[CCN]+TX, copper sulfate (172)+TX, fentin (347)+TX, ferric phosphate(IUPAC name) (352)+TX, metaldehyde (518)+TX, methiocarb (530)+TX,niclosamide (576)+TX, niclosamide-olamine (576)+TX, pentachlorophenol(623)+TX, sodium pentachlorophenoxide (623)+TX, tazimcarb (1412)+TX,thiodicarb (799)+TX, tributyltin oxide (913)+TX, trifenmorph (1454)+TX,trimethacarb (840)+TX, triphenyltin acetate (IUPAC name) (347) andtriphenyltin hydroxide (IUPAC name) (347)+TX, pyriprole[394730-71-3]+TX,

a nematicide selected from the group of substances consisting ofAKD-3088 (compound code)+TX, 1,2-dibromo-3-chloropropane (IUPAC/ChemicalAbstracts name) (1045)+TX, 1,2-dichloropropane (IUPAC/Chemical Abstractsname) (1062)+TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPACname) (1063)+TX, 1,3-dichloropropene (233)+TX,3,4-dichlorotetrahydrothiophene 1,1-dioxide (IUPAC/Chemical Abstractsname) (1065)+TX, 3-(4-chlorophenyl)-5-methylrhodanine (IUPAC name)(980)+TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid (IUPACname) (1286)+TX, 6-isopentenylaminopurine (alternative name) (210)+TX,abamectin (1)+TX, acetoprole [CCN]+TX, alanycarb (15)+TX, aldicarb(16)+TX, aldoxycarb (863)+TX, AZ 60541 (compound code)+TX, benclothiaz[CCN]+TX, benomyl (62)+TX, butylpyridaben (alternative name)+TX,cadusafos (109)+TX, carbofuran (118)+TX, carbon disulfide (945)+TX,carbosulfan (119)+TX, chloropicrin (141)+TX, chlorpyrifos (145)+TX,cloethocarb (999)+TX, cytokinins (alternative name) (210)+TX, dazomet(216)+TX, DBCP (1045)+TX, DCIP (218)+TX, diamidafos (1044)+TX,dichlofenthion (1051)+TX, dicliphos (alternative name)+TX, dimethoate(262)+TX, doramectin (alternative name) [CCN]+TX, emamectin (291)+TX,emamectin benzoate (291)+TX, eprinomectin (alternative name) [CCN]+TX,ethoprophos (312)+TX, ethylene dibromide (316)+TX, fenamiphos (326)+TX,fenpyrad (alternative name)+TX, fensulfothion (1158)+TX, fosthiazate(408)+TX, fosthietan (1196)+TX, furfural (alternative name) [CCN]+TX,GY-81 (development code) (423)+TX, heterophos [CCN]+TX, iodomethane(IUPAC name) (542)+TX, isamidofos (1230)+TX, isazofos (1231)+TX,ivermectin (alternative name) [CCN]+TX, kinetin (alternative name)(210)+TX, mecarphon (1258)+TX, metam (519)+TX, metam-potassium(alternative name) (519)+TX, metam-sodium (519)+TX, methyl bromide(537)+TX, methyl isothiocyanate (543)+TX, milbemycin oxime (alternativename) [CCN]+TX, moxidectin (alternative name) [CCN]+TX, Myrotheciumverrucaria composition (alternative name) (565)+TX, NC-184 (compoundcode)+TX, oxamyl (602)+TX, phorate (636)+TX, phosphamidon (639)+TX,phosphocarb [CCN]+TX, sebufos (alternative name)+TX, selamectin(alternative name) [CCN]+TX, spinosad (737)+TX, terbam (alternativename)+TX, terbufos (773)+TX, tetrachlorothiophene (IUPAC/ChemicalAbstracts name) (1422)+TX, thiafenox (alternative name)+TX, thionazin(1434)+TX, triazophos (820)+TX, triazuron (alternative name)+TX,xylenols [CCN]+TX, YI-5302 (compound code) and zeatin (alternative name)(210)+TX, fluensulfone [318290-98-1]+TX,

a nitrification inhibitor selected from the group of substancesconsisting of potassium ethylxanthate [CCN] and nitrapyrin (580)+TX,

a plant activator selected from the group of substances consisting ofacibenzolar (6)+TX, acibenzolar-S-methyl (6)+TX, probenazole (658) andReynoutria sachalinensis extract (alternative name) (720)+TX,

a rodenticide selected from the group of substances consisting of2-isovalerylindan-1,3-dione (IUPAC name) (1246)+TX,4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748)+TX,alpha-chlorohydrin [CCN]+TX, aluminium phosphide (640)+TX, antu(880)+TX, arsenous oxide (882)+TX, barium carbonate (891)+TX,bisthiosemi (912)+TX, brodifacoum (89)+TX, bromadiolone (91)+TX,bromethalin (92)+TX, calcium cyanide (444)+TX, chloralose (127)+TX,chlorophacinone (140)+TX, cholecalciferol (alternative name) (850)+TX,coumachlor (1004)+TX, coumafuryl (1005)+TX, coumatetralyl (175)+TX,crimidine (1009)+TX, difenacoum (246)+TX, difethialone (249)+TX,diphacinone (273)+TX, ergocalciferol (301)+TX, flocoumafen (357)+TX,fluoroacetamide (379)+TX, flupropadine (1183)+TX, flupropadinehydrochloride (1183)+TX, gamma-HCH (430)+TX, HCH (430)+TX, hydrogencyanide (444)+TX, iodomethane (IUPAC name) (542)+TX, lindane (430)+TX,magnesium phosphide (IUPAC name) (640)+TX, methyl bromide (537)+TX,norbormide (1318)+TX, phosacetim (1336)+TX, phosphine (IUPAC name)(640)+TX, phosphorus [CCN]+TX, pindone (1341)+TX, potassium arsenite[CCN]+TX, pyrinuron (1371)+TX, scilliroside (1390)+TX, sodium arsenite[CCN]+TX, sodium cyanide (444)+TX, sodium fluoro-acetate (735)+TX,strychnine (745)+TX, thallium sulfate [CCN]+TX, warfarin (851) and zincphosphide (640)+TX,

a synergist selected from the group of substances consisting of2-(2-butoxyethoxy)ethyl piperonylate (IUPAC name) (934)+TX,5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903)+TX,farnesol with nerolidol (alternative name) (324)+TX, MB-599 (developmentcode) (498)+TX, MGK 264 (development code) (296)+TX, piperonyl butoxide(649)+TX, piprotal (1343)+TX, propyl isomer (1358)+TX, S421 (developmentcode) (724)+TX, sesamex (1393)+TX, sesasmolin (1394) and sulfoxide(1406)+TX,

an animal repellent selected from the group of substances consisting ofanthraquinone (32)+TX, chloralose (127)+TX, copper naphthenate [CCN]+TX,copper oxychloride (171)+TX, diazinon (227)+TX, dicyclopentadiene(chemical name) (1069)+TX, guazatine (422)+TX, guazatine acetates(422)+TX, methiocarb (530)+TX, pyridin-4-amine (IUPAC name) (23)+TX,thiram (804)+TX, trimethacarb (840)+TX, zinc naphthenate [CCN] and ziram(856)+TX,

a virucide selected from the group of substances consisting of imanin(alternative name) [CCN] and ribavirin (alternative name) [CCN]+TX,

a wound protectant selected from the group of substances consisting ofmercuric oxide (512)+TX, octhilinone (590) and thiophanate-methyl(802)+TX,

and biologically active compounds selected from the group consisting ofazaconazole (60207-31-0]+TX, bitertanol [70585-36-3]+TX, bromuconazole[116255-48-2]+TX, cyproconazole [94361-06-5]+TX, difenoconazole[119446-68-3]+TX, diniconazole [83657-24-3]+TX, epoxiconazole[106325-08-0]+TX, fenbuconazole [114369-43-6]+TX, fluquinconazole[136426-54-5]+TX, flusilazole [85509-19-9]+TX, flutriafol[76674-21-0]+TX, hexaconazole [79983-71-4]+TX, imazalil [35554-44-0]+TX,imibenconazole [86598-92-7]+TX, ipconazole [125225-28-7]+TX, metconazole[125116-23-6]+TX, myclobutanil [88671-89-0]+TX, pefurazoate[101903-30-4]+TX, penconazole [66246-88-6]+TX, prothioconazole[178928-70-6]+TX, pyrifenox [88283-41-4]+TX, prochloraz [67747-09-5]+TX,propiconazole [60207-90-1]+TX, simeconazole [149508-90-7]+TX,tebuconazole [107534-96-3]+TX, tetraconazole [112281-77-3]+TX,triadimefon [43121-43-3]+TX, triadimenol [55219-65-3]+TX, triflumizole[99387-89-0]+TX, triticonazole [131983-72-7]+TX, ancymidol[12771-68-5]+TX, fenarimol [60168-88-9]+TX, nuarimol [63284-71-9]+TX,bupirimate [41483-43-6]+TX, dimethirimol [5221-53-4]+TX, ethirimol[23947-60-6]+TX, dodemorph [1593-77-7]+TX, fenpropidine [67306-00-7]+TX,fenpropimorph [67564-91-4]+TX, spiroxamine [118134-30-8]+TX, tridemorph[81412-43-3]+TX, cyprodinil [121552-61-2]+TX, mepanipyrim[110235-47-7]+TX, pyrimethanil [53112-28-0]+TX, fenpiclonil[74738-17-3]+TX, fludioxonil [131341-86-1]+TX, benalaxyl[71626-11-4]+TX, furalaxyl [57646-30-7]+TX, metalaxyl [57837-19-1]+TX,R-metalaxyl [70630-17-0]+TX, ofurace [58810-48-3]+TX, oxadixyl[77732-09-3]+TX, benomyl [17804-35-2]+TX, carbendazim [10605-21-7]+TX,debacarb [62732-91-6]+TX, fuberidazole [3878-19-1]+TX, thiabendazole[148-79-8]+TX, chlozolinate [84332-86-5]+TX, dichlozoline[24201-58-9]+TX, iprodione [36734-19-7]+TX, myclozoline [54864-61-8]+TX,procymidone [32809-16-8]+TX, vinclozoline [50471-44-8]+TX, boscalid[188425-85-6]+TX, carboxin [5234-68-4]+TX, fenfuram [24691-80-3]+TX,flutolanil [66332-96-5]+TX, mepronil [55814-41-0]+TX, oxycarboxin[5259-88-1]+TX, penthiopyrad [183675-82-3]+TX, thifluzamide[130000-40-7]+TX, guazatine [108173-90-6]+TX, dodine [2439-10-3][112-65-2] (free base)+TX, iminoctadine [13516-27-3]+TX, azoxystrobin[131860-33-8]+TX, dimoxystrobin [149961-52-4]+TX, enestroburin {Proc.BCPC, Int. Congr., Glasgow, 2003, 1, 93}+TX, fluoxastrobin[361377-29-9]+TX, kresoxim-methyl [143390-89-0]+TX, metominostrobin[133408-50-1]+TX, trifloxystrobin [141517-21-7]+TX, orysastrobin[248593-16-0]+TX, picoxystrobin [117428-22-5]+TX, pyraclostrobin[175013-18-0]+TX, ferbam [14484-64-1]+TX, mancozeb [8018-01-7]+TX, maneb[12427-38-2]+TX, metiram [9006-42-2]+TX, propineb [12071-83-9]+TX,thiram [137-26-8]+TX, zineb [12122-67-7]+TX, ziram [137-30-4]+TX,captafol [2425-06-1]+TX, captan [133-06-2]+TX, dichlofluanid[1085-98-9]+TX, fluoroimide [41205-21-4]+TX, folpet [133-07-3]+TX,tolylfluanid [731-27-1]+TX, bordeaux mixture [8011-63-0]+TX,copperhydroxid [20427-59-2]+TX, copperoxychlorid [1332-40-7]+TX,coppersulfat [7758-98-7]+TX, copperoxid [1317-39-1]+TX, mancopper[53988-93-5]+TX, oxine-copper [10380-28-6]+TX, dinocap [131-72-6]+TX,nitrothal-isopropyl [10552-74-6]+TX, edifenphos [17109-49-8]+TX,iprobenphos [26087-47-8]+TX, isoprothiolane [50512-35-1]+TX, phosdiphen[36519-00-3]+TX, pyrazophos [13457-18-6]+TX, tolclofos-methyl[57018-04-9]+TX, acibenzolar-S-methyl [135158-54-2]+TX, anilazine[101-05-3]+TX, benthiavalicarb [413615-35-7]+TX, blasticidin-S[2079-00-7]+TX, chinomethionat [2439-01-2]+TX, chloroneb [2675-77-6]+TX,chlorothalonil [1897-45-6]+TX, cyflufenamid [180409-60-3]+TX, cymoxanil[57966-95-7]+TX, dichlone [117-80-6]+TX, diclocymet [139920-32-4]+TX,diclomezine [62865-36-5]+TX, dicloran [99-30-9]+TX, diethofencarb[87130-20-9]+TX, dimethomorph [110488-70-5]+TX, SYP-LI90 (Flumorph)[211867-47-9]+TX, dithianon [3347-22-6]+TX, ethaboxam [162650-77-3]+TX,etridiazole [2593-15-9]+TX, famoxadone [131807-57-3]+TX, fenamidone[161326-34-7]+TX, fenoxanil [115852-48-7]+TX, fentin [668-34-8]+TX,ferimzone [89269-64-7]+TX, fluazinam [79622-59-6]+TX, fluopicolide[239110-15-7]+TX, flusulfamide [106917-52-6]+TX, fenhexamid[126833-17-8]+TX, fosetyl-aluminium [39148-24-8]+TX, hymexazol[10004-44-1]+TX, iprovalicarb [140923-17-7]+TX, IKF-916 (Cyazofamid)[120116-88-3]+TX, kasugamycin [6980-18-3]+TX, methasulfocarb[66952-49-6]+TX, metrafenone [220899-03-6]+TX, pencycuron[66063-05-6]+TX, phthalide [27355-22-2]+TX, polyoxins [11113-80-7]+TX,probenazole [27605-76-1]+TX, propamocarb [25606-41-1]+TX, proquinazid[189278-12-4]+TX, pyroquilon [57369-32-1]+TX, quinoxyfen[124495-18-7]+TX, quintozene [82-68-8]+TX, sulfur [7704-34-9]+TX,tiadinil [223580-51-6]+TX, triazoxide [72459-58-6]+TX, tricyclazole[41814-78-2]+TX, triforine [26644-46-2]+TX, validamycin [37248-47-8]+TX,zoxamide (RH7281) [156052-68-5]+TX, mandipropamid [374726-62-2]+TX,isopyrazam [881685-58-1]+TX, sedaxane [874967-67-6]+TX,3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid(9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide(dislosed in WO 2007/048556)+TX,3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid(3′,4′,5′-trifluoro-biphenyl-2-yl)-amide (disclosed in WO2006/087343)+TX,[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11Hnaphtho[2,1-b]pyrano[3,4-e]pyran-4-yl]methyl-cyclopropanecarboxylate[915972-17-7]+TX and1,3,5-trimethyl-N-(2-methyl-1-oxopropyl)-N-[3-(2-methylpropyl)-4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]phenyl]-1H-pyrazole-4-carboxamide[926914-55-8]+TX.

The references in brackets behind the active ingredients, e.g.[3878-19-1] refer to the Chemical Abstracts Registry number. The abovedescribed mixing partners are known. Where the active ingredients areincluded in “The Pesticide Manual” [The Pesticide Manual—A WorldCompendium; Thirteenth Edition; Editor: C. D. S. TomLin; The BritishCrop Protection Council], they are described therein under the entrynumber given in round brackets hereinabove for the particular compound;for example, the compound “abamectin” is described under entry number(1). Where “[CCN]” is added hereinabove to the particular compound, thecompound in question is included in the “Compendium of Pesticide CommonNames”, which is accessible on the internet [A. Wood; Compendium ofPesticide Common Names, Copyright © 1995-2004]; for example, thecompound “acetoprole” is described under the internet addresshttp://www.alanwood.net/pesticides/acetoprole.html.

Most of the active ingredients described above are referred tohereinabove by a so-called “common name”, the relevant “ISO common name”or another “common name” being used in individual cases. If thedesignation is not a “common name”, the nature of the designation usedinstead is given in round brackets for the particular compound; in thatcase, the IUPAC name, the IUPAC/Chemical Abstracts name, a “chemicalname”, a “traditional name”, a “compound name” or a “develoment code” isused or, if neither one of those designations nor a “common name” isused, an “alternative name” is employed. “CAS Reg. No” means theChemical Abstracts Registry Number.

The active ingredient mixture of the compounds of formula (I) selectedfrom a compound described in one of Tables 1A to 30A, 1B to 29B, 1C to33C, 1D to 27D or 1E to 27E (below), or one of Tables T1a, T1b, T2a,T2b, T3a, T3b, T4a, T4b, T5a or T5b (below) and an active ingredient asdescribed above are preferably in a mixing ratio of from 100:1 to1:6000, especially from 50:1 to 1:50, more especially in a ratio of from20:1 to 1:20, even more especially from 10:1 to 1:10, very especiallyfrom 5:1 and 1:5, special preference being given to a ratio of from 2:1to 1:2, and a ratio of from 4:1 to 2:1 being likewise preferred, aboveall in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2,or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4,or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000,or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750.Those mixing ratios are by weight.

The mixtures as described above can be used in a method for controllingpests, which comprises applying a composition comprising a mixture asdescribed above to the pests or their environment, with the exception ofa method for treatment of the human or animal body by surgery or therapyand diagnostic methods practised on the human or animal body.

The mixtures comprising a compound of formula (I) selected from one ofTables 1A to 30A, 1B to 29B, 1C to 33C, 1D to 27D or 1E to 27E (below),or one of Tables T1a, T1b, T2a, T2b, T3a, T3b, T4a, T4b, T5a or T5b(below) and one or more active ingredients as described above can beapplied, for example, in a single “ready-mix” form, in a combined spraymixture composed from separate formulations of the single activeingredient components, such as a “tank-mix”, and in a combined use ofthe single active ingredients when applied in a sequential manner, i.e.one after the other with a reasonably short period, such as a few hoursor days. The order of applying the compounds of formula (I) selectedfrom Tables 1A to 30A, 1B to 29B, 1C to 33C, 1D to 27D or 1E to 27E(below), or Tables T1a, T1b, T2a, T2b, T3a, T3b, T4a, T4b, T5a or T5b(below), and the active ingredient(s) as described above, is notessential for working the present invention.

The compositions according to the invention can also comprise furthersolid or liquid auxiliaries, such as stabilizers, for exampleunepoxidized or epoxidized vegetable oils (for example epoxidizedcoconut oil, rapeseed oil or soya oil), antifoams, for example siliconeoil, preservatives, viscosity regulators, binders and/or tackifiers,fertilizers or other active ingredients for achieving specific effects,for example bactericides, fungicides, nematocides, plant activators,molluscicides or herbicides.

The compositions according to the invention are prepared in a mannerknown per se, in the absence of auxiliaries for example by grinding,screening and/or compressing a solid active ingredient and in thepresence of at least one auxiliary for example by intimately mixingand/or grinding the active ingredient with the auxiliary (auxiliaries).These processes for the preparation of the compositions and the use ofthe compounds (I) for the preparation of these compositions are also asubject of the invention.

Another aspect of invention is related to the use of a compound offormula (I) or of a preferred individual compound according to thesegeneral formulae as defined herein, of a composition comprising at leastone compound of formula (I) or at least one preferred individualcompound as defined herein, or of a fungicidal or insecticidal mixturecomprising at least one compound of formula (I) or at least onepreferred individual compound as defined herein, in admixture with otherfungicides or insecticides as described above, for controlling orpreventing infestation of plants (eg, useful plants such as cropplants), propagation material thereof (eg, seeds), harvested crops(e.g., harvested food crops), or non-living materials by insects or byphytopathogenic microorganisms, preferably fungal organisms.

A further aspect of invention is related to a method of controlling orpreventing an infestation of plants, (e.g., useful plants such as cropplants), propagation material thereof (e.g., seeds), harvested crops,(e.g., harvested food crops), or of non-living materials by insects orby phytopathogenic or spoilage microorganisms or organisms potentiallyharmful to man, especially fungal organisms, which comprises theapplication of a compound of formula (I) or of a preferred individualcompound as defined herein as active ingredient to the plants, to partsof the plants or to the locus thereof, to the propagation materialthereof, or to any part of the non-living materials.

Controlling or preventing means of reducing infestation by insects or byphytopathogenic or spoilage microorganisms or organisms potentiallyharmful to man, especially fungal organisms, to such a level that animprovement is demonstrated.

A preferred method of controlling or preventing an infestation of cropplants by phytopathogenic microorganisms, especially fungal organisms,or insects which comprises the application of a compound of formula (I),or an agrochemical composition which contains at least one of saidcompounds, is foliar application. The frequency of application and therate of application will depend on the risk of infestation by thecorresponding pathogen or insect. However, the compounds of formula (I)can also penetrate the plant through the roots via the soil (systemicaction) by drenching the locus of the plant with a liquid formulation,or by applying the compounds in solid form to the soil, e.g. in granularform (soil application). In crops of water rice such granulates can beapplied to the flooded rice field. The compounds of formula (I) may alsobe applied to seeds (coating) by impregnating the seeds or tubers eitherwith a liquid formulation of the fungicide or coating them with a solidformulation.

A formulation, e.g., a composition containing the compound of formula(I), and, if desired, a solid or liquid adjuvant or monomers forencapsulating the compound of formula (I), may be prepared in a knownmanner, typically by intimately mixing and/or grinding the compound withextenders, for example solvents, solid carriers and, optionally, surfaceactive compounds (surfactants).

Advantageous rates of application are normally from 5 g to 2 kg ofactive ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kga.i./ha, most preferably from 20 g to 600 g a.i./ha. When used as seeddrenching agent, convenient dosages are from 10 mg to 1 g of activesubstance per kg of seeds.

When the combinations of the present invention are used for treatingseed, rates of 0.001 to 50 g of a compound of formula (I) per kg ofseed, preferably from 0.01 to 10 g per kg of seed are generallysufficient.

The compositions of the invention may be employed in any conventionalform, for example in the form of a twin pack, a powder for dry seedtreatment (DS), an emulsion for seed treatment (ES), a flowableconcentrate for seed treatment (FS), a solution for seed treatment (LS),a water dispersible powder for seed treatment (WS), a capsule suspensionfor seed treatment (CF), a gel for seed treatment (GF), an emulsionconcentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE),a capsule suspension (CS), a water dispersible granule (WG), anemulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion,oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oilmiscible flowable (OF), an oil miscible liquid (OL), a solubleconcentrate (SL), an ultra-low volume suspension (SU), an ultra-lowvolume liquid (UL), a technical concentrate (TK), a dispersibleconcentrate (DC), a wettable powder (WP) or any technically feasibleformulation in combination with agriculturally acceptable adjuvants.

Such compositions may be produced in conventional manner, e.g. by mixingthe active ingredients with appropriate formulation inerts (diluents,solvents, fillers and optionally other formulating ingredients such assurfactants, biocides, anti-freeze, stickers, thickeners and compoundsthat provide adjuvancy effects). Also conventional slow releaseformulations may be employed where long lasting efficacy is intended.Particularly formulations to be applied in spraying forms, such as waterdispersible concentrates (e.g. EC, SC, DC, OD, SE, EW, EO and the like),wettable powders and granules, may contain surfactants such as wettingand dispersing agents and other compounds that provide adjuvancyeffects, e.g. the ondensation product of formaldehyde with naphthalenesulphonate, an alkylarylsulphonate, a lignin sulphonate, a fatty alkylsulphate, and ethoxylated alkylphenol and an ethoxylated fatty alcohol.

A seed dressing formulation is applied in a manner known per se to theseeds employing the combination of the invention and a diluent insuitable seed dressing formulation form, e.g. as an aqueous suspensionor in a dry powder form having good adherence to the seeds. Such seeddressing formulations are known in the art. Seed dressing formulationsmay contain the single active ingredients or the combination of activeingredients in encapsulated form, e.g. as slow release capsules ormicrocapsules.

In general, the formulations include from 0.01 to 90% by weight ofactive agent, from 0 to 20% agriculturally acceptable surfactant and 10to 99.99% solid or liquid formulation inerts and adjuvant(s), the activeagent consisting of at least the compound of formula (I) together withcomponent (B) and (C), and optionally other active agents, particularlymicrobiocides or conservatives or the like. Concentrated forms ofcompositions generally contain in between about 2 and 80%, preferablybetween about 5 and 70% by weight of active agent. Application forms offormulation may for example contain from 0.01 to 20% by weight,preferably from 0.01 to 5% by weight of active agent. Whereas commercialproducts will preferably be formulated as concentrates, the end userwill normally employ diluted formulations

The examples which follow serve to illustrate the invention. Thecompounds of the invention can be distinguished from known compounds byvirtue of greater efficacy at low application rates, which can beverified by the person skilled in the art using the experimentalprocedures outlined in the Examples, using lower application rates ifnecessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm or 0.8ppm.

Compounds of Formula (I) (including those according to the invention)may possess any number of benefits including, inter alia, advantageouslevels of biological activity for protecting plants against diseasesthat are caused by fungi or superior properties for use as agrochemicalactive ingredients (for example, greater biological activity, anadvantageous spectrum of activity, an increased safety profile(including improved crop tolerance), improved physico-chemicalproperties, or increased biodegradability).

PREPARATION EXAMPLES Example 1

This example illustrates the preparation of2-fluoro-N-(tetrahydropyran-4-ylmethyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide(Compound 1 b. 18 of Table T1 b below)

Step 1: Preparation of 2-fluoro-4-(N-hydroxycarbamimidoyl)-benzoic Acid

A solution of hydroxylamine hydrochloride (3.0 g) in water (20 mL) wasadded at room temperature to a stirred solution of4-cyano-2-fluorobenzoic acid (3.52 g, 21.3 mmol) in ethanol (35 mL),followed by dropwise addition of potassium carbonate (1.60 g). Then8-hydroxyquinoline (0.04 g, 0.28 mmol) was added and the resulting thicksuspension was heated to reflux for 3 hours to obtain a yellow solution.After removal of ethanol under reduced pressure the residue wasacidified with 2N HCl to pH 3. The white precipitate was filtered,washed with water, and dried under reduced pressure at 50° C. to yield2-fluoro-4-(N-hydroxycarbamimidoyl)-benzoic acid as a beige solid.Mp: >250° C. ¹H NMR (400 MHz, DMSO-d6) δ ppm: 13.22 (s, 1H), 10.00 (s,1H), 7.85 (t, 1H), 7.63 (m, 1H), 7.54-7.61 (m, 1H).

Step 2: Preparation of2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic Acid

Trifluoroacetic anhydride (4.1 mL) was added dropwise at 10 to 15° C. toa stirred suspension of 2-fluoro-4-(N-hydroxycarbamimidoyl)-benzoic acid(3.80 g, 19.0 mmol) in THF (77 mL). The beige suspension was warmed toroom temperature and stirred overnight. After evaporation, the crudeproduct was stirred with heptane/ethyl acetate (95:5), filtered anddried under reduced pressure at 50° C. to yield2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as ayellow solid. Mp: 175-177° C. ¹H NMR (400 MHz, DMSO-d₆) δ ppm: 13.55 (s,1H), 8.12 (t, 1H), 8.00 (d, 1H), 7.94 (d, 1H).

Step 3: Preparation of2-fluoro-4-(5-(trifluoromethyl)-[1,2,4]oxadiazol-3-yl)-benzoyl Chloride

To a white suspension consisting of2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid (3.6g, 13.0 mmol) and CH₂Cl₂ (130 mL) at room temperature was added thionylchloride (1.51 mL) dropwise. The resulting suspension was heated toreflux and stirred for 3 hours, to obtain a yellow solution. The solventwas evaporated under reduced pressure at 30° C. to yield2-fluoro-4-(5-(trifluoromethyl)-[1,2,4]oxadiazol-3-yl)-benzoyl chlorideas a yellowish solid that was used directly without purification. ¹H NMR(400 MHz, CDCl₃) δ ppm: 8.26 (t, 1H), 8.07 (m, 1H), 7.99 (m, 1H).

Step 4: Preparation of2-fluoro-N-(tetrahydropyran-4-ylmethyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide

To a screw-cap vial containing2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoyl chloride(0.13 g) suspended in CH₂Cl₂ (12 mL) cooled to 0° C. was addedtetrahydropyran-4-ylmethanamine (0.05 g) as a CH₂Cl₂ (1 mL) solution.Then triethylamine (0.12 mL) was slowly introduced and the resultantyellow solution was stirred overnight. The reaction contents were thenpoured into a separatory funnel and diluted with CH₂Cl₂ and water. Theorganic layer was separated and then washed with 1N HCl, 1N NaOH, brine,and then dried over sodium sulfate. The solvent was removed underreduced pressure and the crude residue was purified by flashchromatography over silica gel (heptane:ethyl acetate gradient) to givethe title compound as a white solid (melting point: 134-136° C.), LC/MSretention time=0.96 minutes, 374.4 (M+H).

Example 2

This example illustrates the preparation ofN-(1-cyano-1-cyclopropyl-ethyl)-2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide(Compound 2b.9 of Table T2b below)

To a screw-cap vial containing 2-amino-2-cyclopropyl-propanenitrile(0.05 g) suspended in CH₂Cl₂ (12 mL) cooled to 0° C. was slowlyintroduced triethylamine (0.12 mL). Then,2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoyl chloride(0.13 g) was added in one portion and the resultant yellow solution wasstirred overnight. The solvent was removed under reduced pressure andthe resultant crude residue was purified by flash chromatography oversilica gel (heptane:ethyl acetate eluent gradient) to give the titlecompound as a yellow oil. LC/MS retention time=1.04 minutes, 369.4(M+H).

Example 3 (Reference)

This example illustrates the preparation ofN-allyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (Compound3a.1 of Table T3a below)

To a stirred solution of 4-5-trifluoromethyl-1,2,4-oxadiazol-3-ylbenzoic acid (0.08 g) in dry DMF (1.2 ml) under an atmosphere ofnitrogen was added N-ethyl-N-isopropylpropan-2-amine (0.14 mL), HATU(0.13 g) and allylamine (0.02 g). The reaction mixture was stirred atroom temperature for 2 hours and then ethyl acetate and water wereadded. The resultant mixture was shaken and the layers were separated.The aqueous layer was extracted twice with ethyl acetate and thecombined organic layers were washed with brine, dried over sodiumsulfate, and filtered. Isolut was added to the filtrate and theresulting mixture was evaporated to dryness and then purified by columnchromatography (cyclohexane:ethyl acetate eluent gradient). The titlecompound was obtained as a white solid (melting point: 135-136° C.),LC/MS retention time=0.95 minutes, 298.2 (M+H).

Example 4

This example illustrates the preparation of2-fluoro-N-[(2-fluorophenyl)methyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide(Compound 4b.1 of Table T4b below)

Step 1: Preparation of 2-fluoro-4-(N-hydroxycarbamimidoyl)-benzoic Acid

A solution of hydroxylamine hydrochloride (3.0 g) in water (20 mL) wasadded at room temperature to a stirred solution of4-cyano-2-fluorobenzoic acid (3.52 g, 21.3 mmol) in ethanol (35 mL),followed by dropwise addition of potassium carbonate (1.60 g). Then8-hydroxyquinoline (0.041 g, 0.28 mmol) was added and the resultingthick suspension was heated to reflux for 3 hours to obtain a yellowsolution. After removal of ethanol under reduced pressure the residuewas acidified with 2N HCl to pH 3. The white precipitate was filtered,washed with water, and dried under reduced pressure at 50° C. to yield2-fluoro-4-(N-hydroxycarbamimidoyl)-benzoic acid as a beige solid.Mp: >250° C. ¹H NMR (400 MHz, DMSO-d6) δ ppm: 13.22 (s, 1H), 10.00 (s,1H), 7.85 (t, 1H), 7.63 (m, 1H), 7.54-7.61 (m, 1H).

Step 2: Preparation of2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic Acid

Trifluoroacetic anhydride (4.1 mL) was added dropwise at 10 to 15° C. toa stirred suspension of 2-fluoro-4-(N-hydroxycarbamimidoyl)-benzoic acid(3.80 g, 19.0 mmol) in THF (77 mL). The beige suspension was warmed toroom temperature and stirred overnight. After evaporation, the crudeproduct was stirred with heptane/ethyl acetate (95:5), filtered anddried under reduced pressure at 50° C. to yield2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as ayellow solid. Mp: 175-177° C. ¹H NMR (400 MHz, DMSO-d₆) δ ppm: 13.55 (s,1H), 8.12 (t, 1H), 8.00 (d, 1H), 7.94 (d, 1H).

Step 3: Preparation of2-fluoro-4-(5-(trifluoromethyl)-[1,2,4]oxadiazol-3-yl)-benzoyl Chloride

To a white suspension consisting of2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid (3.6g, 13.0 mmol) and CH₂Cl₂ (130 mL) at room temperature was added thionylchloride (1.51 mL) dropwise. The resulting suspension was heated toreflux and stirred for 3 hours, to obtain a yellow solution. The solventwas evaporated under reduced pressure at 30° C. to yield2-fluoro-4-(5-(trifluoromethyl)-[1,2,4]oxadiazol-3-yl)-benzoyl chlorideas a yellowish solid that was used directly without purification. ¹H NMR(400 MHz, CDCl₃) δ ppm: 8.26 (t, 1H), 8.07 (m, 1H), 7.99 (m, 1H).

Step 4: Preparation of2-fluoro-N-[(2-fluorophenyl)methyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide

To a screw-cap vial containing2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoyl chloride(0.13 g) suspended in CH₂Cl₂ (1.2 mL) cooled to 0° C. was added(2-fluorophenyl)methanamine (0.60 g) as a CH₂Cl₂ (1 mL) solution. Thentriethylamine (0.12 mL) was slowly introduced and the resultant yellowsolution was stirred for 4 hours. The reaction contents were then pouredinto a seporatory funnel and diluted with CH₂Cl₂ and water. The organiclayer was separated and then washed with 1N HCl, 1N NaOH, and brine. Thesolvent was removed under reduced pressure and the crude residue waspurified by flash chromatography over silica gel (cyclohexane:ethylacetate gradient) to give the title compound as a white solid (mp:132-136° C.). LC/MS retention time=1.08 minutes, 384 (M+H).

Example 5 (Reference)

This example illustrates the preparation ofN-(p-tolylmethyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide(Compound 4a.1 of Table T4a)

To a stirred solution of 4-5-trifluoromethyl-1,2,4-oxadiazol-3-ylbenzoic acid (0.08 g, 0.31 mmol) in dry DMF (1.2 ml) under an atmosphereof nitrogen was added N-ethyl-N-isopropylpropan-2-amine (0.11 g, 0.77mmol), HATU (0.13 g, 0.34 mmol) and 4-methylbenzylamine (0.04 g, 0.31mmol). The reaction mixture was stirred at room temperature for 2 hoursand then ethyl acetate and water were added. The resultant mixture wasshaken and the layers were separated. The aqueous layer was extractedtwice with ethyl acetate and the combined organic layers were washedwith brine, dried over sodium sulfate and filtered. Isolut was added tothe filtrate and the resulting mixture was evaporated to dryness andthen purified by column chromatography (eluent cyclohexane-ethyl acetatemixture mixtures). The title compound was obtained as a white solid,(m.p. 198-203° C.), LC/MS retention time=1.09 minutes, 362 (M+H).

Example 6

This example illustrates the preparation of2-fluoro-N-methyl-N-[(3-methyl-2-thienyl)methyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide(Compound 5b.3 of Table T5b below)

Step 1: Preparation of 2-fluoro-4-(N-hydroxycarbamimidoyl)-benzoic Acid

A solution of hydroxylamine hydrochloride (3.0 g) in water (20 mL) wasadded at room temperature to a stirred solution of4-cyano-2-fluorobenzoic acid (3.52 g, 21.3 mmol) in ethanol (35 mL),followed by dropwise addition of potassium carbonate (1.60 g). Then8-hydroxyquinoline (0.04 g, 0.28 mmol) was added and the resulting thicksuspension was heated to reflux for 3 hours to obtain a yellow solution.After removal of ethanol under reduced pressure the residue wasacidified with 2N HCl to pH 3. The white precipitate was filtered,washed with water, and dried under reduced pressure at 50° C. to yield2-fluoro-4-(N-hydroxycarbamimidoyl)-benzoic acid as a beige solid.Mp: >250° C. ¹H NMR (400 MHz, DMSO-d6) δ ppm: 13.22 (s, 1H), 10.00 (s,1H), 7.85 (t, 1H), 7.63 (m, 1H), 7.54-7.61 (m, 1H).

Step 2: Preparation of2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic Acid

Trifluoroacetic anhydride (4.1 mL) was added dropwise at 10 to 15° C. toa stirred suspension of 2-fluoro-4-(N-hydroxycarbamimidoyl)-benzoic acid(3.80 g, 19.0 mmol) in THF (77 mL). The beige suspension was warmed toroom temperature and stirred overnight. After evaporation, the crudeproduct was stirred with heptane/ethyl acetate (95:5), filtered anddried under reduced pressure at 50° C. to yield2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as ayellow solid. Mp: 175-177° C. ¹H NMR (400 MHz, DMSO-d₆) δ ppm: 13.55 (s,1H), 8.12 (t, 1H), 8.00 (d, 1H), 7.94 (d, 1H).

Step 3: Preparation of2-fluoro-4-(5-(trifluoromethyl)-[1,2,4]oxadiazol-3-yl)-benzoyl Chloride

To a white suspension consisting of2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid (3.6g, 13.0 mmol) and CH₂Cl₂ (130 mL) at room temperature was added thionylchloride (1.51 mL) dropwise. The resulting suspension was heated toreflux and stirred for 3 hours, to obtain a yellow solution. The solventwas evaporated under reduced pressure at 30° C. to yield2-fluoro-4-(5-(trifluoromethyl)-[1,2,4]oxadiazol-3-yl)-benzoyl chlorideas a yellowish solid that was used directly without purification. ¹H NMR(400 MHz, CDCl₃) δ ppm: 8.26 (t, 1H), 8.07 (m, 1H), 7.99 (m, 1H).

Step 4: Preparation of2-fluoro-N-methyl-N-[(3-methyl-2-thienyl)methyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide

To a screw-cap vial containing2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoyl chloride(0.13 g) suspended in CH₂Cl₂ (1.2 mL) cooled to 0° C. was addedN-methyl-1-(3-methyl-2-thienyl)methanamine hydrochloride (0.08 g) as aCH₂Cl₂ (1 mL) solution. Then triethylamine (0.25 mL) was slowlyintroduced and the resultant yellow solution was stirred for 14 hours.The reaction contents were then poured into a separatory funnel anddiluted with CH₂Cl₂ and water. The organic layer was separated and thenwashed with 1N HCl, 1N NaOH, and brine. The solvent was removed underreduced pressure and the crude residue was purified by flashchromatography over silica gel (cyclohexane:ethyl acetate gradient) togive the title compound as a yellow oil. LC/MS retention time=1.13minutes, 400.4 (M+H).

HATU=1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium3-oxid-hexafluorophosphate

TABLE 1A This table discloses 78 specific compounds of formula (T-1A)(T-1A)

  wherein R¹ and R³ are hydrogen, R² is fluorine and R⁴ or R^(4A) (whenR⁴ is R^(4A)) is as defined below in the table No. R⁴/R^(4A) 1.001tetrahydropyran-2-yl 1.002 tetrahydropyran-3-yl 1.003tetrahydropyran-4-yl 1.004 3-methyltetrahydropyran-3-yl 1.0054-methyltetrahydropyran-4-yl 1.006 (tetrahydropyran-2-yl)methyl 1.007(tetrahydropyran-2-yl)ethyl 1.008 1-(tetrahydropyran-2-yl)ethyl 1.009(tetrahydropyran-3-yl)methyl 1.010 (tetrahydropyran-3-yl)ethyl 1.0111-(tetrahydropyran-3-yl)ethyl 1.012 (tetrahydropyran-4-yl)methyl 1.013(tetrahydropyran-4-yl)ethyl 1.014 1-(tetrahydropyran-4-yl)ethyl 1.015tetrahydrofuran-2-yl 1.016 tetrahydrofuran-3-yl 1.017(tetrahydrofuran-3-yl)methyl 1.018 (tetrahydrofuran-2-yl)methyl 1.019(tetrahydrofuran-2-yl)ethyl 1.020 1-(tetrahydrofuran-2-yl)ethyl 1.021(tetrahydrofuran-3-yl)methyl 1.022 (tetrahydrofuran-3-yl)ethyl 1.0231-(tetrahydrofuran-3-yl)ethyl 1.024 2-methylisoxazolidin-4-yl 1.0251-(2-methylisoxazolidin-4-yl)ethyl 1.026 1-methoxypiperidin-4-yl 1.027(l-methoxypiperidin-4-yl)methyl 1.028 1-(1-methoxypiperidin-4-yl)ethyl1.029 1-methoxy-4-cyano-piperidin-4-yl 1.0301-methoxy-4-methyl-piperidin-4-yl 1.031 4-methyl carboxylate1-methoxypiperidin-4-yl 1.032 (2,6-dimethylpiperidin-1-yl)methyl 1.033(2,6-dimethylpiperidin-1-yl)ethyl 1.034 3-methyl carboxylate1-methoxypiperidin-3-yl 1.035 (1-methyl-piperidin-2-yl)methyl 1.0361-ethyl carboxylate piperidin-4-yl 1.037 1-tert-butyl carboxylatepiperidin-4-yl 1.038 1-methylpiperidylin-4-yl 1.0391-benzylpiperidin-4-yl 1.040 1-ethyl carboxylate piperidin-3-yl 1.0411-methylpiperidin-3-yl 1.042 1-ethylpiperidin-3-yl 1.0431-benzylpiperidin-3-yl 1.044 (1-ethyl carboxylate piperidin-3-yl)methyl1.045 (1-tert-butyl carboxylate piperidin-3-yl)methyl 1.046(1-methylpiperidin-3-yl)methyl 1.047 (1-ethylpiperidin-3-yl)methyl 1.048(1-benzylpiperidin-3-yl)methyl 1.049 1-ethyl carboxylate pyrrolidin-3-yl1.050 1-tert-butyl carboxylate pyrrolidin-3-yl 1.0511-methylpyrrolidin-3-yl 1.052 1-ethylpyrrolidin-3-yl 1.0531-benzyl-pyrrolidin-3-yl 1.054 (1-ethyl carboxylatepyrrolidin-3-yl)methyl 1.055 (1-tert butyl carboxylatepyrrolidin-3-yl)methyl 1.056 (1-methylpyrrolidin-3-yl)methyl 1.057(1-ethylpyrrolidin-3-yl)methyl 1.058 (1-benzyl-pyrrolidin-3-yl)methyl1.059 (1-piperldyl)ethyl 1.060 1-(1-piperidyl)propyl 1.061(1,4-dioxan-2-yl)methyl 1.062 (1,4-dioxan-2-yl)ethyl 1.0631-(1,4-dioxan-2-yl)ethyl 1.064 tetrahydrothiopyran-3-yl 1.065(tetrahydrothiopyran-3-yl)methyl 1.066 tetrahydrothiopyran-4-yl 1.067(tetrahydrothiopyran-4-yl)methyl 1.068 tetrahydrothiophen-3-yl 1.069(tetrahydrothiophen-3-yl)methyl 1.070 1,3-dioxolan-2-yl)methyl 1.0711-(1,3-dioxolan-2-yl)ethyl 1.072 (2,2-dimethyl-1,3-dioxolan-4-yl)methyl1.073 1-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl 1.074(2-methyl-1,3-dioxolan-2-yl)methyl 1.0751-(2-methyl-1,3-dioxolan-2-yl)ethyl 1.076(2-methyl-1,3-dioxolan-2-yl)methyl 1.0771-(2-methyl-1,3-dioxolan-2-yl)ethyl 1.078 1-tert-butyl carboxylatepiperidin-3-ylTable 2A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ is hydrogen, R² is fluorine, R³ is methyl and R^(4A) is asdefined above in Table 1A.Table 3A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ is hydrogen, R² is fluorine, R³ is ethyl and R^(4A) is asdefined above in Table 1A.Table 4A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ is hydrogen, R² is fluorine, R³ is ethyl and R^(4A) is asdefined above in Table 1A.Table 5A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ and R³ are hydrogen, R² is chlorine and R^(4A) is as definedabove in Table 1A.Table 6A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ is hydrogen, R² is chlorine, R³ is methyl and R^(4A) is asdefined above in Table 1A.Table 7A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ is hydrogen, R² is chlorine, R³ is ethyl and R^(4A) is asdefined above in Table 1A.Table 8A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ and R³ are hydrogen, R² is methyl and R^(4A) is as definedabove in Table 1A.Table 9A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ is hydrogen, R² is methyl, R³ is methyl and R^(4A) is asdefined above in Table 1A.Table 10A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ is hydrogen, R² is methyl, R³ is ethyl and R^(4A) is asdefined above in Table 1A.Table 11A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ and R³ are hydrogen, R² is methoxy and R^(4A) is as definedabove in Table 1A.Table 12A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ is hydrogen, R² is methoxy, R³ is methyl and R^(4A) is asdefined above in Table 1A.Table 13A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ is hydrogen, R² is methoxy, R³ is ethyl and R^(4A) is asdefined above in Table 1A.Table 14A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ is hydrogen, R² is fluorine, R³ is isopropyl and R^(4A) is asdefined above in Table 1A.Table 15A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹, R² and R³ are hydrogen and R⁴ is as defined above in Table1A.Table 16A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹, R² are hydrogen, R³ is methyl and R⁴ is as defined above inTable 1A.Table 17A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹, R² are hydrogen, R³ is ethyl and R⁴ is as defined above inTable 1A.Table 18A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ and R² are fluorine, R³ is hydrogen and R⁴ is as definedabove in Table 1A.Table 19A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ and R² are fluorine, R³ is methyl and R⁴ is as defined abovein Table 1A.Table 20A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ and R² are fluorine, R³ is ethyl and R⁴ is as defined abovein Table 1A.Table 21A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ and R² are chlorine, R³ are hydrogen and R⁴ is as definedabove in Table 1A.Table 22A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ and R² are chlorine, R³ is methyl and R⁴ is as defined abovein Table 1A.Table 23A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ and R² are chlorine, R³ is ethyl and R⁴ is as defined abovein Table 1A.Table 24A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ and R² are methyl, R³ is hydrogen and R⁴ is as defined abovein Table 1A.Table 25A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ and R² are methyl, R³ is methyl and R⁴ is as defined above inTable 1A.Table 26A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ and R² are methyl, R³ is ethyl and R⁴ is as defined above inTable 1A.Table 27A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ and R² are methoxy, R³ is hydrogen and R⁴ is as defined abovein Table 1A.Table 28A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ and R² are methoxy, R³ is methyl and R⁴ is as defined abovein Table 1A.Table 29A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ and R² are methoxy, R³ is ethyl and R⁴ is as defined above inTable 1A.Table 30A: This table discloses 78 specific compounds of formula (T-1A)wherein R¹ and R² are hydrogen, R³ is isopropyl and R⁴ is as definedabove in Table 1A.

TABLE 1B This table discloses 43 specific compounds of formula (T-1B)(T-1B)

wherein R¹ and R³ are hydrogen, R² is fluorine, and R⁴ or R^(4B) (whenR⁴ is R^(4B)) is as defined below in the table No. R⁴/R^(4B) 1.001cyclopropyl 1.002 cyclobutyl 1.003 cyclopentyl 1.004 cyclohexyl 1.005cycloheptyl 1.006 cyclooctyl 1.007 (cyclopropyl)methyl 1.008(cyclobutyl)methyl 1.009 (cyclopentyl)methyl 1.010 (cyclohexyl)methyl1.011 (cycloheptyl)methyl 1.012 1-(cycloctyl)ethyl 1.0131-(cyclopropyl)ethyl 1.014 1-(cyclobutyl)ethyl 1.0151-(cyclopentyl)ethyl 1.016 1-(cyclohexyl)ethyl 1.0171-(cycloheptyl)ethyl 1.018 1-(cycloctyl)ethyl 1.0191-cyclopropylcyclopropyl 1.020 1-cyanocyclopropyl 1.021(1-cyanocyclopropyl)methyl 1.022 1-cyanocyclopropyl 1.0231-(cyano-1-cyclopropyl)ethyl 1.024 2,2-difluorocyclopentyl 1.0251-((4-chlorophenyl)methyl)cyclopropyl 1.026 2-phenylcyclopropyl 1.0272,2,3,3-tetrafluorocyclobutyl 1.028(2,2,3,3-tetrafluorocyclobutyl)methyl 1.029 1-methylcyclobutyl 1.0302-methylcyclobuty 1.031 2,2-dimethylcyclobutyl 1.0322,2-difluorocyclobutyl 1.033 2-cyanocyclobutyl 1.034 1-methylcyclopentyl1.035 2,2-difluorocyclopentyl 1.036 3,3-difluorocyclopentyl 1.0372-methylcyclopentyl 1.038 2,2-dimethylcyclopentyl 1.0392-methylcyclohexyl 1.040 3-methylcyclohexyl 1.041 4-methylcyclohexyl1.042 4,4-dimethylcyclohexyl 1.043 1-ethynylcyclohexylTable 2B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ is hydrogen, R² is fluorine, R³ is methyl and R^(4B) is asdefined above in Table 1B.Table 3B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ is hydrogen, R² is fluorine, R³ is ethyl and R^(4B) is asdefined above in Table 1B.Table 4B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ and R³ are hydrogen, R² is chlorine and R^(4B) is as definedabove in Table 1B.Table 5B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ is hydrogen, R² is chlorine, R³ is methyl and R^(4B) is asdefined above in Table 1B.Table 6B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ is hydrogen, R² is chlorine, R³ is ethyl and R^(4B) is asdefined above in Table 1B.Table 7B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ and R³ are hydrogen, R² is methyl and R^(4B) is as definedabove in Table 1B.Table 8B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ is hydrogen, R² is methyl, R³ is methyl and R^(4B) is asdefined above in Table 1B.Table 9B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ is hydrogen, R² is methyl, R³ is ethyl and R^(4B) is asdefined above in Table 1B.Table 10B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ and R³ are hydrogen, R² is methoxy and R^(4B) is as definedabove in Table 1B.Table 11B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ is hydrogen, R² is methoxy, R³ is methyl and R^(4B) is asdefined above in Table 1B.Table 12B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ is hydrogen, R² is methoxy, R³ is ethyl and R^(4B) is asdefined above in Table 1B.Table 13B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ is hydrogen, R² is fluorine, R³ is isopropyl and R^(4B) is asdefined above in Table 1B.Table 14B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹, R² and R³ are hydrogen and R⁴ is as defined above in thetable in Table 1B.Table 15B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹, R² are hydrogen, R³ is methyl and R⁴ is as defined above inTable 1B.Table 16B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹, R² are hydrogen, R³ is ethyl and R⁴ is as defined above inTable 1B.Table 17B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ and R² are fluorine, R³ is hydrogen and R⁴ is as definedabove in Table 1B.Table 18B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ and R² are fluorine, R³ is methyl and R⁴ is as defined abovein Table 1B.Table 19B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ and R² are fluorine, R³ is ethyl and R⁴ is as defined abovein Table 1B.Table 20B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ and R² are chlorine, R³ is hydrogen and R⁴ is as definedabove in Table 1B.Table 21B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ and R² are chlorine, R³ is methyl and R⁴ is as defined abovein Table 1B.Table 22B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ and R² are chlorine, R³ is ethyl and R⁴ is as defined abovein Table 1B.Table 23B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ and R² are methyl, R³ is hydrogen and R⁴ is as defined abovein Table 1B.Table 24B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ and R² are methyl, R³ is methyl and R⁴ is as defined above inTable 1B.Table 25B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ and R² are methyl, R³ is ethyl and R⁴ is as defined above inTable 1B.Table 26B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ and R² are methoxy, R³ is hydrogen and R⁴ is as defined abovein Table 1B.Table 27B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ and R² are methoxy, R³ is methyl and R⁴ is as defined abovein Table 1B.Table 28B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ and R² are methoxy, R³ is ethyl and R⁴ is as defined above inTable 1B.Table 29B: This table discloses 43 specific compounds of formula (T-1B)wherein R¹ and R² are hydrogen, R³ is an isopropyl and R⁴ is as definedabove in Table 1B.

TABLE 1C This table discloses 113 specific compounds of formula (T-1C)(T-1C)

wherein R¹ and R³ are hydrogen, R² is fluorine and R⁴ or R^(4C) (when R⁴is R^(4C)) is as defined below in the table No. R⁴/R^(4C) 1.001 methyl1.002 ethyl 1.003 propyl 1.004 butyl 1.005 pentyl 1.006 hexyl 1.007iso-propyl 1.008 sec-butyl 1.009 iso-butyl 1.010 tert-butyl 1.0113,3-dimethylpropyl 1.012 4-methylpentyl 1.013 1-methylpentyl 1.0141,3-dimethylbutyl 1.015 2-ethylbutyl 1.016 2-propenyl 1.017 2-butenyl1.018 3-butenyl 1.019 2-methyl-2-propenyl 1.020 2-pentenyl 1.0213-pentenyl 1.022 4-pentenyl 1.023 1-methyl-2-butenyl 1.0242-methyl-2-butenyl 1.025 3-methyl-2-butenyl 1.026 1-methyl-3-butenyl1.027 2-methyl-3-butenyl 1.028 3-methyl-3-butenyl 1.0291,1-dimethyl-2-propenyl 1.030 1,2-dimethyl-2-propenyl, 1.0311-ethyl-2-propenyl 1.032 1-hexenyl 1.033 2-hexenyl 1.034 3-hexenyl 1.0354-hexenyl 1.036 5-hexenyl 1.037 1-methyl-4-pentenyl 1.0382-methyl-4-pentenyl 1.039 3-methyl-4-pentenyl 1.040 4-methyl-4-pentenyl1.041 1,1-dimethyl-2-butenyl 1.042 1,1-dimethyl-3-butenyl 1.0431,2-dimethyl-2-butenyl 1.044 1,2-dimethyl-3-butenyl 1.0451,3-dimethyl-2-butenyl 1.046 1,3-dimethyl-3-butenyl 1.047 2-propynyl1.048 2-butynyl 1.049 3-butynyl 1.050 1-methyl-2-propynyl 1.0512-pentynyl 1.052 3-pentynyl 1.053 4-pentynyl 1.054 1-methyl-2-butynyl1.055 1-methyl-3-butynyl 1.056 2-methyl-3-butynyl 1.0571,1-dimethyl-2-propynyl 1.058 1-ethyl-2-propynyl 1.059 2-hexynyl 1.0603-hexynyl 1.061 4-hexynyl 1.062 5-hexynyl 1.063 2-methoxyethyl 1.0642-ethoxyethyl 1.065 2-propoxyethyl 1.066 2-iso-propoxyethyl 1.0672-butoxyethyl 1.068 2-sec-butoxyethyl 1.069 2-tert-butoxyethyl 1.0702-methoxypropyl 1.071 2-ethoxypropyl 1.072 2-propoxypropyl 1.0732-iso-propoxypropyl 1.074 2-butoxypropyl 1.075 2-sec-butoxypropyl 1.0762-tert-butoxypropyl 1.077 3-methoxypropyl 1.078 3-ethoxypropyl 1.0793-propoxypropyl 1.080 3-iso-propoxypropyl 1.081 3-butoxypropyl 1.0823-sec-butoxypropyl 1.083 3-tert-butoxypropyl 1.0841-(methoxymethyl)propyl 1.085 1-(methoxymethyl)ethyl 1.0862-hydroxypropyl 1.087 3-hydroxypropyl 1.088 1-hydroxybutyl 1.0892-hydroxybutyl 1.090 3-hydroxybutyl 1.091 4-hydroxybutyl 1.0922-hydroxybutyl 1.093 5-hydroxypentyl 1.094 1-(hydroxymethyl)-isopropyl1.095 2-hydroxy-2-methyl-propyl 1.096 3-hydroxy-1,1-dimethyl-propyl1.097 2-hydroxybutyl 1.098 3-hydroxy-1-methyl-propyl 1.0991,1-dimethylprop-2-ynyl 1.100 2-chloroethyl 1.101 3-chloropropyl 1.1024-chlorobutyl 1.103 1-fluoroethyl 1.104 2-fluoroethyl 1.1051-fluoropropyl 1.106 2-fluoropropyl 1.107 3-fluoropropyl 1.1084-fluorobutyl 1.109 2-(tert-butylamino)-2-oxo-ethyl 1.1102-(iso-propylamino)-2-oxo-ethyl 1.111 2-(ethylamino)-2-oxo-ethyl 1.1122-acetamidoethyl 1.113 ethyl 3-butanoateTable 2C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ is hydrogen, R² is fluorine, R³ is methyl and R^(4C) is asdefined above in Table 1C.Table 3C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ is hydrogen, R² is fluorine, R³ is ethyl and R^(4C) is asdefined above in Table 1C.Table 4C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ and R³ are hydrogen, R² is chlorine and R^(4C) is as definedabove in Table 1C.Table 5C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ is hydrogen, R² is chlorine, R³ is methyl and R^(4C) is asdefined above in Table 1C.Table 9C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ is hydrogen, R² is chlorine, R³ is ethyl and R^(4C) is asdefined above in Table 1C.Table 10C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ and R³ are hydrogen, R² is methyl and R^(4C) is as definedabove in Table 1C.Table 11C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ is hydrogen, R² is methyl, R³ is methyl and R^(4C) is asdefined above in Table 1C.Table 12C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ is hydrogen, R² is methyl, R³ is ethyl and R^(4C) is asdefined above in Table 1C.Table 13C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ and R³ are hydrogen, R² is methoxy and R^(4C) is as definedabove in Table 1C.Table 14C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ is hydrogen, R² is methoxy, R³ is methyl and R^(4C) is asdefined above in Table 1C.Table 15C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ is hydrogen, R² is methoxy, R³ is ethyl and R^(4C) is asdefined above in Table 1C.Table 16C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ is hydrogen, R² is fluorine, R³ is isopropyl and R^(4C) is asdefined above in Table 1C.Table 17C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ is hydrogen, R² is chlorine, R³ is isopropyl and R^(4C) is asdefined above in Table 1C.Table 18C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹, R² and R³ are hydrogen and R⁴ is as defined above in thetable in Table 1C.Table 19C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹, R² are hydrogen, R³ is methyl and R⁴ is as defined above inTable 1C.Table 20C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹, R² are hydrogen, R³ is ethyl and R⁴ is as defined above inTable 1C.Table 21C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ and R² are fluorine, R³ is hydrogen and R⁴ is as definedabove in Table 1C.Table 22C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ and R² are fluorine, R³ is methyl and R⁴ is as defined abovein Table 1C.Table 23C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ and R² are fluorine, R³ is ethyl and R⁴ is as defined abovein Table 1C.Table 24C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ and R² are chlorine, R³ is hydrogen and R⁴ is as definedabove in Table 1C.Table 25C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ and R² are chlorine, R³ is methyl and R⁴ is as defined abovein Table 1C.Table 26C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ and R² are chlorine, R³ is ethyl and R⁴ is as defined abovein Table 1C.Table 27C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ and R² are methyl, R³ is hydrogen and R⁴ is as defined abovein Table 1C.Table 28C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ and R² are methyl, R³ is methyl and R⁴ is as defined above inTable 1C.Table 29C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ and R² are methyl, R³ is ethyl and R⁴ is as defined above inTable 1C.Table 30C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ and R² are methoxy, R³ is hydrogen and R⁴ is as defined abovein Table 1C.Table 31C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ and R² are methoxy, R³ is methyl and R⁴ is as defined abovein Table 1C.Table 32C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ and R² are methoxy, R³ is ethyl and R⁴ is as defined above inTable 1C.Table 33C: This table discloses 113 specific compounds of formula (T-1C)wherein R¹ and R² are hydrogen, R³ is isopropyl and R⁴ is as definedabove in Table 1C.

TABLE 1D This table discloses 174 specific compounds of formula (T-1D)(T-1D)

wherein R¹ and R³ are hydrogen, R² is fluorine and R⁴ or R^(4D) (when R⁴is R^(4D)) is as defined below in the table No. R⁴/R^(4D) 1.0012-fluorophenyl 1.002 3-fluorophenyl 1.003 4-fluorophenyl 1.0042-chlorophenyl 1.005 3-chlorophenyl 1.006 4-chlorophenyl 1.0072-bromophenyl 1.008 3-bromophenyl 1.009 4-bromophenyl 1.0102-cyanophenyl 1.011 3-cyanophenyl 1.012 4-cyanophenyl 1.0132-methylphenyl 1.014 3-methylphenyl 1.015 4-methylphenyl 1.0162-ethylphenyl 1.017 3-ethylphenyl 1.018 4-ethylphenyl 1.0192-trifluorophenyl 1.020 3-trifluorophenyl 1.021 4-trifluorophenyl 1.0222-methoxyphenyl 1.023 3-methoxyphenyl 1.024 4-methoxyphenyl 1.0252-ethoxyphenyl 1.026 3-ethoxyphenyl 1.027 4-ethoxyphenyl 1.0282-ethynylphenyl 1.029 3-ethynylphenyl 1.030 4-ethynylphenyl 1.0312-phenylphenyl 1.032 3-phenylphenyl 1.033 4-phenylphenyl 1.0342-cyclopropylphenyl 1.035 3-cyclopropylphenyl 1.036 4-cyclopropylphenyl1.037 2,3-difluorophenyl 1.038 2,4-difluorophenyl 1.0392,5-difluorophenyl 1.040 2,6-difluorophenyl 1.041 3,4-difluorophenyl1.042 3,5-difluorophenyl 1.043 2,3-dichlorophenyl 1.0442,4-dichlorophenyl 1.045 2,5-dichlorophenyl 1.046 2,6-dichlorophenyl1.047 3,4-dichlorophenyl 1.048 3,5-dichlorophenyl 1.0492-fluoro-3-cyanophenyl 1.050 2-fluoro-4-cyanophenyl 1.0512-fluoro-5-cyanophenyl 1.052 2-fluoro-6-cyanophenyl 1.0533-fluoro-2-cyanophenyl 1.054 3-fluoro-4-cyanophenyl 1.0553-fluoro-5-cyanophenyl 1.056 3-fluoro-6-cyanophenyl 1.0574-fluoro-2-cyanophenyl 1.058 4-fluoro-3-cyanophenyl 1.059 2-fluorobenzyl1.060 3-fluorobenzyl 1.061 4-fluorobenzyl 1.062 2-chlorobenzyl 1.0633-chlorobenzyl 1.064 4-chlorobenzyl 1.065 2-bromobenzyl 1.0663-bromobenzyl 1.067 4-bromobenzyl 1.068 2-cyanobenzyl 1.0693-cyanobenzyl 1.070 4-cyanobenzyl 1.071 2-methylbenzyl 1.0723-methylbenzyl 1.073 4-methylbenzyl 1.074 2-ethylbenzyl 1.0753-ethylbenzyl 1.076 4-ethylbenzyl 1.077 2-trifluorobenzyl 1.0783-trifluorobenzyl 1.079 4-trifluorobenzyl 1.080 2-methoxybenzyl 1.0813-methoxybenzyl 1.082 4-methoxybenzyl 1.083 2-ethoxybenzyl 1.0843-ethoxybenzyl 1.085 4-ethoxybenzyl 1.086 2-ethynylbenzyl 1.0873-ethynylbenzyl 1.088 4-ethynylbenzyl 1.089 2-phenylbenzyl 1.0903-phenylbenzyl 1.091 4-phenylbenzyl 1.092 2-cyclopropylbenzyl 1.0933-cyclopropylbenzyl 1.094 4-cyclopropylbenzyl 1.095 2,3-difluorobenzyl1.096 2,4-difluorobenzyl 1.097 2,5-difluorobenzyl 1.0982,6-difluorobenzyl 1.099 3,4-difluorobenzyl 1.100 3,5-difluorobenzyl1.101 2,3-dichlorobenzyl 1.102 2,4-dichlorobenzyl 1.1032,5-dichlorobenzyl 1.104 2,6-dichlorobenzyl 1.105 3,4-dichlorobenzyl1.106 3,5-dichlorobenzyl 1.107 2-fluoro-3-cyanobenzyl 1.1082-fluoro-4-cyanobenzyl 1.109 2-fluoro-5-cyanobenzyl 1.1102-fluoro-6-cyanobenzyl 1.111 3-fluoro-2-cyanobenzyl 1.1123-fluoro-4-cyanobenzyl 1.113 3-fluoro-5-cyanobenzyl 1.1143-fluoro-6-cyanobenzyl 1.115 4-fluoro-2-cyanobenzyl 1.1164-fluoro-3-cyanobenzyl 1.117 2-fluorophenethyl 1.118 3-fluorophenethyl1.119 4-fluorophenethyl 1.120 2-chlorophenethyl 1.121 3-chlorophenethyl1.122 4-chlorophenethyl 1.123 2-bromophenethyl 1.124 3-bromophenethyl1.125 4-bromophenethyl 1.126 2-cyanophenethyl 1.127 3-cyanophenethyl1.128 4-cyanophenethyl 1.129 2-methylphenethyl 1.130 3-methylphenethyl1.131 4-methylphenethyl 1.132 2-ethylphenethyl 1.133 3-ethylphenethyl1.134 4-ethylphenethyl 1.135 2-trifluorophenethyl 1.1363-trifluorophenethyl 1.137 4-trifluorophenethyl 1.138 2-methoxyphenethyl1.139 3-methoxyphenethyl 1.140 4-methoxyphenethyl 1.1412-ethoxyphenethyl 1.142 3-ethoxyphenethyl 1.143 4-ethoxyphenethyl 1.1442-ethynylphenethyl 1.145 3-ethynylphenethyl 1.146 4-ethynylphenethyl1.147 2-phenylphenethyl 1.148 3-phenylphenethyl 1.149 4-phenylphenethyl1.150 2-cyclopropylphenethyl 1.151 3-cyclopropylphenethyl 1.1524-cyclopropylphenethyl 1.153 2,3-difluorophenethyl 1.1542,4-difluorophenethyl 1.155 2,5-difluorophenethyl 1.1562,6-difluorophenethyl 1.157 3,4-difluorophenethyl 1.1583,5-difluorophenethyl 1.159 2,3-dichlorophenethyl 1.1602,4-dichlorophenethyl 1.161 2,5-dichlorophenethyl 1.1622,6-dichlorophenethyl 1.163 3,4-dichlorophenethyl 1.1643,5-dichlorophenethyl 1.165 2-fluoro-3-cyanophenethyl 1.1662-fluoro-4-cyanophenethyl 1.167 2-fluoro-5-cyanophenethyl 1.1682-fluoro-6-cyanophenethyl 1.169 3-fluoro-2-cyanophenethyl 1.1703-fluoro-4-cyanophenethyl 1.171 3-fluoro-5-cyanophenethyl 1.1723-fluoro-6-cyanophenethyl 1.173 4-fluoro-2-cyanophenethyl 1.1744-fluoro-3-cyanophenethylTable 2D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹ is hydrogen, R² is fluorine, R³ is methyl and R^(4D) is asdefined above in Table 1D.Table 3D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹ is hydrogen, R² is fluorine, R³ is ethyl and R^(4D) is asdefined above in Table 1D.Table 4D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹ and R³ are hydrogen, R² is chlorine and R^(4D) is as definedabove in Table 1D.Table 5D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹ is hydrogen, R² is chlorine, R³ is methyl and R^(4D) is asdefined above in Table 1D.Table 6D: This table discloses 174 specific compounds of formula (T-1D)wherein R is hydrogen, R² is chlorine, R³ is ethyl and R^(4D) is asdefined above in Table 1D.Table 7D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹ is hydrogen, R² is methyl, R³ is hydrogen and R^(4D) is asdefined above in Table 1D.Table 8D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹ is hydrogen, R² is methyl, R³ is methyl and R^(4D) is asdefined above in Table 1D.Table 9D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹ is hydrogen, R² is methyl, R³ is ethyl and R^(4D) is asdefined above in Table 1D.Table 10D: This table discloses 174 specific compounds of formula (T-1D) wherein R¹ is hydrogen, R² is methoxy, R³ are hydrogen and R^(4D) isas defined above in Table 1D.Table 11D: This table discloses 174 specific compounds of formula (T-1D) wherein R¹ is hydrogen, R² is methoxy, R³ is methyl and R^(4D) is asdefined above in Table 1D.Table 12D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹ is hydrogen, R² is methoxy, R³ is ethyl and R^(4D) is asdefined above in Table 1D.Table 13D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹, R² and R³ are hydrogen and R⁴ is as defined above in Table1D.Table 14D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹, R² are hydrogen, R³ is methyl and R⁴ is as defined above inTable 1D.Table 15D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹, R² are hydrogen, R³ is ethyl and R⁴ is as defined above inTable 1D.Table 16D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹ and R² are fluorine, R³ is hydrogen and R⁴ is as definedabove in Table 1D.Table 17D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹ and R² are fluorine, R³ is methyl and R⁴ is as defined abovein Table 1D.Table 18D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹ and R² are fluorine, R³ is ethyl and R⁴ is as defined abovein Table 1D.Table 19D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹ and R² are chlorine, R³ is hydrogen and R⁴ is as definedabove in Table 1D.Table 20D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹ and R² are chlorine, R³ is methyl and R⁴ is as defined abovein Table 1D.Table 21D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹ and R² are chlorine, R³ is ethyl and R⁴ is as defined abovein Table 1D.Table 22D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹ and R² are methyl, R³ is hydrogen and R⁴ is as defined abovein Table 1D.Table 23D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹ and R² are methyl, R³ is methyl and R⁴ is as defined above inTable 1D.Table 24D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹ and R² are methyl, R³ is ethyl and R⁴ is as defined above inTable 1D.Table 25D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹ and R² are methoxy, R³ is hydrogen and R⁴ is as defined abovein Table 1D.Table 26D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹ and R² are methoxy, R³ is methyl and R⁴ is as defined abovein Table 1D.Table 27D: This table discloses 174 specific compounds of formula (T-1D)wherein R¹ and R² are methoxy, R³ is ethyl and R⁴ is as defined above inTable 1D.

TABLE 1E This table discloses 219 specific compounds of formula (T-1E)(T-1E)

wherein R¹ and R³ are hydrogen, R² is fluorine R⁴ or R^(4E) (when R⁴ isR^(4E)) is as defined below in the table No. R⁴/R^(4E) 1.001 2-thienyl1.002 5-fluoro-2-thienyl 1.003 3,5-difluoro-2-thienyl 1.0042,5-difluoro-3-thienyl 1.005 5-chloro-2-thienyl 1.0063,5-dichloro-2-thienyl 1.007 2,5-dichloro-3-thienyl 1.0085-methyl-2-thienyl 1.009 3,5-dimethyl-2-thienyl 1.0102,5-dimethyl-3-thienyl 1.011 5-cyano-2-thienyl 1.012 2-pyridyl 1.0136-fluoro-2-pyridyl 1.014 5-fluoro-2-pyridyl 1.015 4-fluoro-2-pyridyl1.016 3-fluoro-2-pyridyl 1.017 6-chloro-2-pyridyl 1.0185-chloro-2-pyridyl 1.019 4-chloro-2-pyridyl 1.020 3-chloro-2-pyridyl1.021 6-methyl-2-pyridyl 1.022 5-methyl-2-pyridyl 1.0234-methyl-2-pyridyl 1.024 3-methyl-2-pyridyl 1.025 6-cyano-2-pyridyl1.026 5-cyano-2-pyridyl 1.027 4-cyano-2-pyridyl 1.028 3-cyano-2-pyridyl1.029 3,4-difluoro-2-pyridyl 1.030 3,5-difluoro-2-pyridyl 1.0313,6-difluoro-2-pyridyl 1.032 3,4-dichloro-2-pyridyl 1.0333,5-dichloro-2-pyridyl 1.034 3,6-dichloro-2-pyridyl 1.0353-chloro-5-fluoro-2-pyridyl 1.036 5-chloro-3-fluoro-2-pyridyl 1.0373-chloro-5-trifluoromethyl-2-pyridyl 1.038 6-fluoro-3-pyridyl 1.0395-fluoro-3-pyridyl 1.040 4-fluoro-3-pyridyl 1.041 2-fluoro-3-pyridyl1.042 6-chloro-3-pyridyl 1.043 5-chloro-3-pyridyl 1.0444-chloro-3-pyridyl 1.045 2-chloro-3-pyridyl 1.046 6-methyl-3-pyridyl1.047 5-methyl-3-pyridyl 1.048 4-methyl-3-pyridyl 1.0492-methyl-3-pyridyl 1.050 6-cyano-3-pyridyl 1.051 5-cyano-3-pyridyl 1.0524-cyano-3-pyridyl 1.053 2-cyano-3-pyridyl 1.054 4,5-difluoro-3-pyridyl1.055 4,6-difluoro-3-pyridyl 1.056 2,4-difluoro-3-pyridyl 1.0572,5-difluoro-3-pyridyl 1.058 2,6-difluoro-3-pyridyl 1.0594,5-dichloro-3-pyridyl 1.060 4,6-dichloro-3-pyridyl 1.0612,4-dichloro-3-pyridyl 1.062 2,5-dichloro-3-pyridyl 1.0632,6-dichloro-3-pyridyl 1.064 6-fluoro-4-pyridyl 1.065 5-fluoro-4-pyridyl1.066 2-fluoro-4-pyridyl 1.067 6-chloro-4-pyridyl 1.0685-chloro-4-pyridyl 1.069 2-chloro-4-pyridyl 1.070 6-methyl-4-pyridyl1.071 5-methyl-4-pyridyl 1.072 2-methyl-4-pyridyl 1.0736-cyano-4-pyridyl 1.074 5-cyano-4-pyridyl 1.075 2-cyano-4-pyridyl 1.0763,5-difluoro-4-pyridyl 1.077 3,6-difluoro-4-pyridyl 1.0783,5-dichloro-4-pyridyl 1.079 3,6-dichloro-4-pyridyl 1.080 4-pyrimidinyl1.081 5-pyrimidinyl 1.082 5-fluoro-pyrimidinyl 1.0835-chloro-pyrimidinyl 1.084 5-methyl-pyrimidinyl 1.0855-methyl-pyrimidinyl 1.086 2-thiazolyl 1.087 5-fluoro-2-thiazolyl 1.0885-chloro-2-thiazolyl 1.089 5-methyl2-thiazolyl 1.090 5-cyano-2-thiazolyl1.091 1H-imidazol-5-yl 1.092 2-methyl-1H-imidazol-5-yl 1.0932-cyano-1H-imidazol-5-yl 1.094 5-methyl-1H-imidazol-2-yl 1.0955-cyano-1H-imidazol-2-yl 1.096 1,2-dimethylimidazol-5-yl 1.0972-cyano-1-methyl-imidazol-5-yl 1.098 1,5-dimethylimidazol-2-yl 1.0995-cyano-1-methyl-imidazol-2-yl 1.100 oxazol-2-yl 1.101 oxazol-5-yl 1.1022-methyloxazol-5-yl 1.103 2-cyanooxazol-5-yl 1.104 5-methyloxazol-2-yl1.105 5-cyanooxazol-5-yl 1.106 2-methyl-1,2,4-triazol-3-yl 1.107(2-thienyl)methyl 1.108 (2-thienyl)methyl 1.109(5-fluoro-2-thienyl)methyl 1.110 (3,5-difluoro-2-thienyl)methyl 1.111(2,5-difluoro-3-thienyl)methyl 1.112 (5-chloro-2-thienyl)methyl 1.113(3,5-dichloro-2-thienyl)methyl 1.114 (2,5-dichloro-3-thienyl)methyl1.115 (5-methyl-2-thienyl)methyl 1.116 (3,5-dimethyl-2-thienyl)methyl1.117 (2,5-dimethyl-3-thienyl)methyl 1.118 (5-cyano-2-thienyl)methyl1.119 (2-pyridyl)methyl 1.120 (3-pyridyl)methyl 1.121 (4-pyridyl)methyl1.122 (6-fluoro-2-pyridyl)methyl 1.123 (5-fluoro-2-pyridyl)methyl 1.124(4-fluoro-2-pyridyl)methyl 1.125 (3-fluoro-2-pyridyl)methyl 1.126(6-chloro-2-pyridyl)methyl 1.127 (5-chloro-2-pyridyl)methyl 1.128(4-chloro-2-pyridyl)methyl 1.129 (3-chloro-2-pyridyl)methyl 1.130(6-methyl-2-pyridyl)methyl 1.131 (5-methyl-2-pyridyl)methyl 1.132(4-methyl-2-pyridyl)methyl 1.133 (3-methyl-2-pyridyl)methyl 1.134(6-cyano-2-pyridyl)methyl 1.135 (5-cyano-2-pyridyl)methyl 1.136(4-cyano-2-pyridyl)methyl 1.137 (3-cyano-2-pyridyl)methyl 1.138(3,4-difluoro-2-pyridyl)methyl 1.139 (3,5-difluoro-2-pyridyl)methyl1.140 (3,6-difluoro-2-pyridyl)methyl 1.141(3,4-dichloro-2-pyridyl)methyl 1.142 (3,5-dichloro-2-pyridyl)methyl1.143 (3,6-dichloro-2-pyridyl)methyl 1.144(3-chloro-5-fluoro-2-pyridyl)methyl 1.145(5-chloro-3-fluoro-2-pyridyl)methyl 1.146(3-chloro-5-trifluoromethyl-2-pyridyl)methyl 1.147(6-fluoro-3-pyridyl)methyl 1.148 (5-fluoro-3-pyridyl)methyl 1.149(4-fluoro-3-pyridyl)methyl 1.150 (2-fluoro-3-pyridyl)methyl 1.151(6-chloro-3-pyridyl)methyl 1.152 (5-chloro-3-pyridyl)methyl 1.153(4-chloro-3-pyridyl)methyl 1.154 (2-chloro-3-pyridyl)methyl 1.155(6-methyl-3-pyridyl)methyl 1.156 (5-methyl-3-pyridyl)methyl 1.157(4-methyl-3-pyridyl)methyl 1.158 (2-methyl-3-pyridyl)methyl 1.159(6-cyano-3-pyridyl)methyl 1.160 (5-cyano-3-pyridyl)methyl 1.161(4-cyano-3-pyridyl)methyl 1.162 (2-cyano-3-pyridyl)methyl 1.163(4,5-difluoro-3-pyridyl)methyl 1.164 (4,6-difluoro-3-pyridyl)methyl1.165 (2,4-difluoro-3-pyridyl)methyl 1.166(2,5-difluoro-3-pyridyl)methyl 1.167 (2,6-difluoro-3-pyridyl)methyl1.168 (4,5-dichloro-3-pyridyl)methyl 1.169(4,6-dichloro-3-pyridyl)methyl 1.170 (2,4-dichloro-3-pyridyl)methyl1.171 (2,5-dichloro-3-pyridyl)methyl 1.172(2,6-dichloro-3-pyridyl)methyl 1.173 (6-fluoro-4-pyridyl)methyl 1.174(5-fluoro-4-pyridyl)methyl 1.175 (3-fluoro-4-pyridyl)methyl 1.176(2-fluoro-4-pyridyl)methyl 1.177 (6-chloro-4-pyridyl)methyl 1.178(5-chloro-4-pyridyl)methyl 1.179 (3-chloro-4-pyridyl)methyl 1.180(2-chloro-4-pyridyl)methyl 1.181 (6-methyl-4-pyridyl)methyl 1.182(5-methyl-4-pyridyl)methyl 1.183 (3-methyl-4-pyridyl)methyl 1.184(2-methyl-4-pyridyl)methyl 1.185 (6-cyano-4-pyridyl)methyl 1.186(5-cyano-4-pyridyl)methyl 1.187 (3-cyano-4-pyridyl)methyl 1.188(2-cyano-4-pyridyl)methyl 1.189 (3,5-difluoro-4-pyridyl)methyl 1.190(3,6-difluoro-4-pyridyl)methyl 1.191 (3,5-dichloro-4-pyridyl)methyl1.192 (3,6-dichloro-4-pyridyl)methyl 1.193 (4-pyrimidinyl)methyl 1.194(5-pyrimidinyl)methyl 1.195 (5-fluoro-pyrimidinyl)methyl 1.196(5-chloro-pyrimidinyl)methyl 1.197 (5-methyl-pyrimidinyl)methyl 1.198(5-methyl-pyrimidinyl)methyl 1.199 (2-thiazolyl)methyl 1.200(5-fluoro-2-thiazolyl)methyl 1.201 (5-chloro-2-thiazolyl)methyl 1.202(5-methyl2-thiazolyl)methyl 1.203 (5-cyano-2-thiazolyl)methyl 1.204(1H-imidazol-5-yl)methyl 1.205 (2-methyl-1H-imidazol-5-yl)methyl 1.206(2-cyano-1H-imidazol-5-yl)methyl 1.207 (5-methyl-1H-imidazol-2-yl)methyl1.208 (5-cyano-1H-imidazol-2-yl)methyl 1.209(1,2-dimethylimidazol-5-yl)methyl 1.210(2-cyano-1-methyl-imidazol-5-yl)methyl 1.211(1,5-dimethylimidazol-2-yl)methyl 1.212(5-cyano-1-methyl-imidazol-2-yl)methyl 1.213 (oxazol-2-yl)methyl 1.214(oxazol-5-yl)methyl 1.215 (2-methyloxazol-5-yl)methyl 1.216(2-cyanooxazol-5-yl)methyl 1.217 (5-methyloxazol-2-yl)methyl 1.218(5-cyanooxazol-5-yl)methyl 1.219 (2-methyl-1,2,4-triazol-3-yl)methylTable 2E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ is hydrogen, R² is fluorine, R³ is methyl and R^(4E) is asdefined above in Table 1E.Table 3E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ is hydrogen, R² is fluorine, R³ is ethyl and R^(4E) is asdefined above in Table 1E.Table 4E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ is hydrogen, R² is chlorine, R³ is hydrogen and R^(4E) is asdefined above in Table 1E.Table 5E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ is hydrogen, R² is chlorine, R³ is methyl and R^(4E) is asdefined above in Table 1E.Table 6E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ is hydrogen, R² is chlorine, R³ is ethyl and R^(4E) is asdefined above in Table 1E.Table 7E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ is hydrogen, R² is methyl, R³ is hydrogen and R^(4E) is asdefined above in Table 1E.Table 8E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ is hydrogen, R² is methyl, R³ is methyl and R^(4E) is asdefined above in Table 1E.Table 9E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ is hydrogen, R² is methyl, R³ is ethyl and R^(4E) is asdefined above in Table 1E.Table 10E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ is hydrogen, R² is methoxy, R³ is hydrogen and R^(4E) is asdefined above in Table 1E.Table 11E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ is hydrogen, R² is methoxy, R³ is methyl and R^(4E) is asdefined above in Table 1E.Table 12E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ is hydrogen, R² is methoxy, R³ is ethyl and R^(4E) is asdefined above in Table 1E.Table 13E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹, R² and R³ are hydrogen and R⁴ is as defined above in Table1E.Table 14E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹, R² are hydrogen, R³ is methyl and R⁴ is as defined above inTable 1E Table 15E: This table discloses 219 specific compounds offormula (T-1E) wherein R¹, R² are hydrogen, R³ is ethyl and R⁴ is asdefined above in Table 1E.Table 16E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ and R² are fluorine, R³ is hydrogen and R⁴ is as definedabove in Table 1E.Table 17E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ and R² are fluorine, R³ is methyl and R⁴ is as defined abovein Table 1E.Table 18E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ and R² are fluorine, R³ is ethyl and R⁴ is as defined abovein Table 1E.Table 19E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ and R² are chlorine, R³ is hydrogen and R⁴ is as definedabove in Table 1E.Table 20E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ and R² are chlorine, R³ is methyl and R⁴ is as defined abovein Table 1E.Table 21E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ and R² are chlorine, R³ is ethyl and R⁴ is as defined abovein Table 1E.Table 22E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ and R² are methyl, R³ is hydrogen and R⁴ is as defined abovein Table 1E.Table 23E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ and R² are methyl, R³ is methyl and R⁴ is as defined above inTable 1E.Table 24E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ and R² are methyl, R³ is ethyl and R⁴ is as defined above inTable 1E.Table 25E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ and R² are methoxy, R³ is hydrogen and R⁴ is as defined abovein Table 1E.Table 26E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ and R² are methoxy, R³ is methyl and R⁴ is as defined abovein Table 1E.Table 27E: This table discloses 219 specific compounds of formula (T-1E)wherein R¹ and R² are methoxy, R³ is ethyl and R⁴ is as defined above inTable 1E.

Throughout this description, temperatures are given in degrees Celsius(° C.) and “m.p.” means melting point. LC/MS means Liquid ChromatographyMass Spectrometry and the description of the apparatus and the methods(A and B) used for LC/MS analysis are given below.

The Description of the Apparatus and the Method A is:

SQ Detector 2 from Waters

Ionisation method: Electrospray

Polarity: positive and negative ions

Capillary (kV) 3.0, Cone (V) 30.00, Extractor (V) 2.00, SourceTemperature (° C.) 150, Desolvation Temperature (° C.) 350, Cone GasFlow (L/Hr) 0, Desolvation Gas Flow (L/Hr) 650

Mass range: 100 to 900 Da

DAD Wavelength range (nm): 210 to 500

Method Waters ACQUITY UPLC with the Following HPLC Gradient Conditions

(Solvent A: Water/Methanol 20:1+0.05% formic acid and Solvent B:Acetonitrile+0.05% formic acid)

Time (minutes) A (%) B (%) Flow rate (ml/min) 0 100 0 0.85 1.2 0 1000.85 1.5 0 100 0.85

Type of column: Waters ACQUITY UPLC HSS T3; Column length: 30 mm;Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron;Temperature: 60° C.

The Description of the Apparatus and the Method B is:

SQ Detector 2 from Waters

Ionisation method: Electrospray

Polarity: positive ions

Capillary (kV) 3.5, Cone (V) 30.00, Extractor (V) 3.00, SourceTemperature (° C.) 150, Desolvation Temperature (° C.) 400, Cone GasFlow (L/Hr) 60, Desolvation Gas Flow (L/Hr) 700

Mass range: 140 to 800 Da

DAD Wavelength range (nm): 210 to 400

Method Waters ACQUITY UPLC with the Following HPLC Gradient Conditions

(Solvent A: Water/Methanol 9:1+0.1% formic acid and Solvent B:Acetonitrile+0.1% formic acid)

Time (minutes) A (%) B (%) Flow rate (ml/min) 0 100 0 0.75 2.5 0 1000.75 2.8 0 100 0.75 3.0 100 0 0.75Type of column: Waters ACQUITY UPLC HSS T3; Column length: 30 mm;Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron;Temperature: 60° C.

Where necessary, enantiomerically pure final compounds may be obtainedfrom racemic materials as appropriate via standard physical separationtechniques, such as reverse phase chiral chromatography, or throughstereoselective synthetic techniques, eg, by using chiral startingmaterials.

FORMULATION EXAMPLES

Wettable powders a) b) c) active ingredient [compound of formula (I)]25%  50% 75% sodium lignosulfonate 5%  5% — sodium lauryl sulfate 3% — 5% sodium diisobutylnaphthalenesulfonate —  6% 10% phenol polyethyleneglycol ether —  2% — (7-8 mol of ethylene oxide) highly dispersedsilicic acid 5% 10% 10% Kaolin 62%  27% —

The active ingredient is thoroughly mixed with the adjuvants and themixture is thoroughly ground in a suitable mill, affording wettablepowders that can be diluted with water to give suspensions of thedesired concentration.

Powders for dry seed treatment a) b) c) active ingredient [compound offormula (I)] 25% 50% 75% light mineral oil  5%  5%  5% highly dispersedsilicic acid  5%  5% — Kaolin 65% 40% — Talcum — 20%

The active ingredient is thoroughly mixed with the adjuvants and themixture is thoroughly ground in a suitable mill, affording powders thatcan be used directly for seed treatment.

Emulsifiable concentrate active ingredient [compound of formula (I)] 10%octylphenol polyethylene glycol ether  3% (4-5 mol of ethylene oxide)calcium dodecylbenzenesulfonate  3% castor oil polyglycol ether (35 molof ethylene oxide)  4% Cyclohexanone 30% xylene mixture 50%

Emulsions of any required dilution, which can be used in plantprotection, can be obtained from this concentrate by dilution withwater.

Dusts a) b) c) Active ingredient [compound of formula (I)]  5%  6%  4%Talcum 95% — — Kaolin — 94% — mineral filler — — 96%

Ready-for-use dusts are obtained by mixing the active ingredient withthe carrier and grinding the mixture in a suitable mill. Such powderscan also be used for dry dressings for seed.

Extruded granules Active ingredient [compound of formula (I)] 15% sodiumlignosulfonate  2% Carboxymethylcellulose  1% Kaolin 82%

The active ingredient is mixed and ground with the adjuvants, and themixture is moistened with water. The mixture is extruded and then driedin a stream of air.

Coated granules Active ingredient [compound of formula (I)] 8%polyethylene glycol (mol. wt. 200) 3% Kaolin 89% 

The finely ground active ingredient is uniformly applied, in a mixer, tothe kaolin moistened with polyethylene glycol. Non-dusty coated granulesare obtained in this manner.

Suspension concentrate active ingredient [compound of formula (I)] 40%propylene glycol 10% nonylphenol polyethylene glycol ether (15 mol ofethylene oxide)  6% Sodium lignosulfonate 10% Carboxymethylcellulose  1%silicone oil (in the form of a 75% emulsion in water)  1% Water 32%

The finely ground active ingredient is intimately mixed with theadjuvants, giving a suspension concentrate from which suspensions of anydesired dilution can be obtained by dilution with water. Using suchdilutions, living plants as well as plant propagation material can betreated and protected against infestation by microorganisms, byspraying, pouring or immersion.

Flowable concentrate for seed treatment active ingredient [compound offormula (I)] 40%  propylene glycol 5% copolymer butanol PO/EO 2%tristyrenephenole with 10-20 moles EO 2% 1,2-benzisothiazolin-3-one (inthe form of 0.5%  a 20% solution in water) monoazo-pigment calcium salt5% Silicone oil (in the form of a 75% emulsion in water) 0.2%  Water45.3%  

The finely ground active ingredient is intimately mixed with theadjuvants, giving a suspension concentrate from which suspensions of anydesired dilution can be obtained by dilution with water. Using suchdilutions, living plants as well as plant propagation material can betreated and protected against infestation by microorganisms, byspraying, pouring or immersion.

Slow Release Capsule Suspension

28 parts of a combination of the compound of formula (I) are mixed with2 parts of an aromatic solvent and 7 parts of toluenediisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1). Thismixture is emulsified in a mixture of 1.2 parts of polyvinylalcohol,0.05 parts of a defoamer and 51.6 parts of water until the desiredparticle size is achieved. To this emulsion a mixture of 2.8 parts1,6-diaminohexane in 5.3 parts of water is added. The mixture isagitated until the polymerization reaction is completed.

The obtained capsule suspension is stabilized by adding 0.25 parts of athickener and 3 parts of a dispersing agent. The capsule suspensionformulation contains 28% of the active ingredients. The medium capsulediameter is 8-15 microns. The resulting formulation is applied to seedsas an aqueous suspension in an apparatus suitable for that purpose.

TABLE T1a Melting point (mp) data and/or retention times (R_(t)) forcompounds according to Formula (I). Mass Table R_(t) charge mp EntryCompound name Structure (mins) (M + H)⁺ Method (° C.) 1a.1 tert-butyl3-[methyl- [4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]benzoyl]amino] pyrrolidine-1- carboxylate

1.77 441.2 B 1a.2 N-(1,4-dioxan-2- ylmethyl)-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.35 358.1 B 1a.3 N-(1-methoxy-4- piperidyl)-N-methyl-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

0.98 385.4 A 1a.4 N-ethyl-N-(1- methoxy-4- piperidyl)-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

1.03 399.4 A 1a.5 N-(1-methoxy-4- piperidyl)-N-propyl-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

1.08 413.3 A 1a.6 N-[(3S)-1- benzylpyrrolidin-3- yl]-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

1.11 417.0 B 1a.7 N-methyl-N- tetrahydrofuran-3-yl-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

1.41 342.2 B 1a.8 methyl 1-methoxy-3- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzoyl]amino] piperidine-3- carboxylate

1.52 429.2 B 1a.9 N-methyl-N- tetrahydrothiophen- 3-yl-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

1.64 358.2 B 1a.10 N-methyl-N-[(1- methyl-2- piperidyl)methyl]-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

0.95 383.0 B 1a.11 tert-butyl 4-[[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzoyl]amino] methyl]piperidine-1- carboxylate

1.82 455.3 B

TABLE T1b Melting point (mp) data and/or retention times (R_(t)) forcompounds according to Formula (I) when R⁴ is R^(4A): Mass Table R_(t)charge mp Entry Compound name Structure (mins) (M + H)⁺ Method (° C.)1b.1 N-[[(2R)-1- ethylpyrrolidin-2- yl]methyl]-2-fluoro-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

0.98 387.2 B 1b.2 N-(1,3-dioxolan-2- ylmethyl)-2-fluoro-N- methyl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.51 376.2 B 1b.3 N-(1-benzyl-4- piperidyl)-2-fluoro-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

1.09 448.9 B 1b.4 ethyl 4-[[2-fluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzoyl]amino] piperidine-1-carboxylate

1.64 431.2 B 1b.5 2-fluoro-N- tetrahydrothiopyran-3- yl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.75 376.1 B 1b.6 N-[(2,2-dimethyl-1,3- dioxolan-4-yl)methyl]-2-fluoro-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.6 390.2 B 1b.7 2-fluoro-N-methyl-N- tetrahydrofuran-3-yl-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

1.47 360.2 B 1b.8 2-fluoro-N-methyl-N- tetrahydrothiophen-3- yl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.69 376.1 B 1b.9 N-(1,4-dioxan-2- ylmethyl)-2-fluoro-N- methyl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.5 390.2 B 1b.10 2-fluoro-N-methyl-N- (tetrahydropyran-2-ylmethyl)-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.77 388.2 B 1b.11 2-fluoro-N- tetrahydrothiophen-3- yl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.64 362.1 B 1b.12 2-fluoro-N-[1-(2- methyl-1,3-dioxolan-2-yl)ethyl]-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.61 390.2 B 1b.13 2-chloro-N-(1,4- dioxan-2-ylmethyl)-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

0.73 392.0 B 1b.14 2-chloro-N- (tetrahydrofuran-3- ylmethyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

0.74 376.0 B 1b.15 2-fluoro-N-(5-methyl- 4,5-dihydroisoxazol-3-yl)-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

0.91 359.2 A 152.5- 155.9  1b.16 2-fluoro-N- (tetrahydrofuran-3-ylmethyl)-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.41 360.1 B 124.2- 126.2  1b.17 2-fluoro-N- (tetrahydrofuran-2-ylmethyl)-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

0.95 360.0 A 95.6- 96.7  1b.18 2-fluoro-N- (tetrahydropyran-4-ylmethyl)-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

0.96 374.0 A 134-  135.4

TABLE T2a Melting point (mp) data and/or retention times (R_(t)) forcompounds according to Formula (I). Mass Table R_(t) charge mp EntryCompound name Structure (mins) (M + H)⁺ Method (° C.) 2a.1 N-(cyclopropylmethyl)- N-propyl-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.84 354.1 B 2a.2 N-(3- methylcyclohexyl)-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.87 354.2 B 2a.3 N-(cyclobutylmethyl)- 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.71 326.2 B 2a.4 N-(1- methylcyclobutyl)-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.71 326.2 B 2a.5 N-cyclooctyl-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.97 368.2 B 2a.6 N-(4- methylcyclohexyl)-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.9 354.2 B 2a.7 N-[1-[(4- chlorophenyl)methyl] cyclopropyl]-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.93 422.2 B 2a.8 N-[(1R)-1- cyclohexylethyl]-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.97 368.2 B 2a.9 N-(2,2- difluorocyclopentyl)-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.62 361.9 B

TABLE T2b Melting point (mp) data and/or retention times (R_(t)) forcompounds according to Formula (I) when R⁴ is R^(4B). Mass Table R_(t)charge mp Entry Compound name Structure (mins) (M + H)⁺ Method (° C.)2b.1 N- (cyclopropylmethyl)-2- fluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.03 330.0 A 113.5- 114.7  2b.2 N-(1- ethynylcyclohexyl)-2- fluoro-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.87 382.1 B 2b.3 N-cyclobutyl-2-fluoro- 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.64 330.1 B 2b.4 2-fluoro-N-[(2,2,3,3- tetrafluorocyclobutyl)methyl]-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

2.46 416.0 B 2b.5 N-(1- cyclopropylethyl)-2- fluoro-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.73 344.1 B 2b.6 N-(1- cyclopropyl- cyclopropyl)- 2-fluoro-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.73 356.1 B 2b.7 2-fluoro-N-(2- phenylcyclopropyl)-4-5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

1.84 392.1 B 2b.8 N- (cyclopentylmethyl)-2- fluoro-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.13 358.0 A 122-  125.6 2b.9 N-(1-cyano-1- cyclopropyl-ethyl)-2-fluoro-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.05 369.0 A 2b.10 2-fluoro-N-(3- methylcyclohexyl)-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

2b.11 N-(cyclobutylmethyl)- 2-fluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.78 344.2 B 2b.12 2-fluoro-N-(1- methylcyclobutyl)-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

1.79 344.2 B 2b.13 2-chloro-N- (cyclopropylmethyl)-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

0.87 345.9 B 2b.14 2-chloro-N-[(2,2,3,3- tetrafluorocyclobutyl)methyl]-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

2b.15 2-chloro-N-(1- cyclopropylethyl)-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

0.93 359.9 B 2b.16 2-chloro-N-(1- cyclopropyl- cyclopropyl)- 4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

2b.17 N-(2,2- difluorocyclopentyl)-2- fluoro-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.68 379.9 B

TABLE T3a Melting point (mp) data and/or retention times (R_(t)) forcompounds according to Formula (I). Mass Table R_(t) charge mp EntryCompound name Structure (mins) (M + H)⁺ Method (° C.) 3a.1 N-allyl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

0.95 298.3 A 135- 146  3a.2 N-prop-2-ynyl-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

0.88 296.0 A 168.5- 170   3a.3 N-[2-(tert-butylamino)-2-oxo-ethyl]-N-methyl- 4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl]benzamide

1.49 385.3 A 3a.4 methyl 2-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]benzoyl]amino] acetate

1.32 330.1 A 165- 166  3a.5 N-(1,1-dimethylbut-2- ynyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.05 338.0 A  104- 105.1 3a.6 N-(3-hydroxypropyl)- N-methyl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.26 330.1 B 3a.7 N-sec-butyl-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.64 314.1 B 3a.8 N-(3-hydroxy-2,2- dimethyl-propyl)-N- methyl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.54 358.2 B 3a.9 N-[1- (methoxymethyl) propyl]-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.58 344.1 B 3a.10 N-(2-hydroxypropyl)- 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.25 316.0 B 3a.11 N-(2-ethoxypropyl)-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.58 344.0 B 3a.12 N-isopropyl-N-(2- methoxyethyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.68 358.2 B 3a.13 N-isobutyl-N-methyl- 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.75 328.1 B 3a.14 N-(2-hydroxybutyl)-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.35 330.1 B 3a.15 N-(3-hydroxy-1- methyl-propyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.31 330.1 B 3a.16 N-(1,1-dimethyl-3- oxo-butyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.6 356.0 B 3a.17 N-(2-hydroxy-1,1- dimethyl-ethyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.4 330.0 B 130- 135  3a.18 N-[1-(hydroxymethyl)- 2-methyl-propyl]-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.45 344.0 B 3a.19 N-(4-hydroxybutyl)-N- methyl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.30 344.1 B 3a.20 N-(4-chlorobutyl)-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.64 347.9 B 3a.21 N-(5-hydroxypentyl)- 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.33 344.1 B 3a.22 N-(3-ethoxypropyl)-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.56 344.0 B 3a.23 N,N-diisobutyl-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

2.05 370.3 B 3a.24 N-(4-hydroxybutyl)-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.26 330.2 B 3a.25 N-butyl-N-(2- hydroxyethyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.54 358.2 B 3a.26 ethyl 3-[[4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]benzoyl]amino] butanoate

1.60 372.0 B 3a.27 N-(2-hydroxy-2- methyl-propyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.32 330.0 B 3a.28 N-allyl-N-ethyl-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.71 326.1 B 3a.29 N-hexyl-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]benzamide

1.90 342.0 B 3a.30 N,N-diethyl-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.63 314.1 B 3a.31 N-ethyl-N-(2- methylallyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.81 340.0 B 3a.32 N-tert-butyl-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.71 314.1 B 3a.33 N-methyl-N-propyl-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.64 314.1 B 3a.34 N-ethyl-N-isopropyl-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.73 328.1 B 3a.35 N-tert-butyl-N-methyl- 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.82 328.0 B 3a.36 N-butyl-N-methyl-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.76 328.1 B 3a.37 N-(2-methoxy-1- methyl-ethyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.48 330.1 B 3a.38 N-isopentyl-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.77 328.1 B 3a.39 N-(2-ethylbutyl)-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.87 342.2 B 3a.40 N-(2-isopropoxyethyl)- 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.59 344.0 B 3a.41 N-methyl-N-prop-2- ynyl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.52 310.0 B 3a.42 N-(3-hydroxy-1,1- dimethyl-propyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.44 344.0 B 3a.43 N-[2- (difluoromethoxy)-1- methyl-ethyl]-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

128- 130  3a.44 N-[2- (difluoromethoxy)ethyl]- N-methyl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

3a.45 N-[2- (difluoromethoxy)ethyl]- 4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

117- 120 

TABLE T3b Melting point (mp) data and/or retention times (R_(t)) forcompounds according to Formula (I) when R⁴ is R^(4C). Mass Table R_(t)charge mp Entry Compound name Structure (mins) (M + H)⁺ Method (° C.)3b.1  2-fluoro-N-propyl-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]benzamide

1.01 318.3 A 118.5-119.9 3b.2  N-ethyl-2-fluoro-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

0.96 304.3 A 125-127 3b.3  N-allyl-2-fluoro-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.00 316.3 A   108-109.3 3b.4  2-fluoro-N-prop-2- ynyl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

0.96 314.3 A 128.2-129.4 3b.5  2-fluoro-N-isobutyl-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

1.07 332.4 A 126.6-128.3 3b.6  2-fluoro-N-(2- methoxyethyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

0.94 334.3 A 87.6-89   3b.7  N-(1,3-dimethylbutyl)- 2-fluoro-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.9  360.1 B 108.5-110.4 3b.8  N-(1,1-dimethylprop-2-ynyl)-2-fluoro-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]benzamide

1.04 342.0 A 69.2-69.7 3b.9  2-fluoro-N-(3- hydroxypropyl)-N-methyl-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.3  348.0 B 3b.10 2-fluoro-N-sec-butyl- 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.71 332.1 B 3b.11 2-fluoro-N-[1- (methoxymethyl) propyl]-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.66 362.1 B 3b.12 N-(2-ethoxypropyl)-2- fluoro-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.68 362.0 B 3b.13 2-fluoro-N-isopropyl- N-(2-methoxyethyl)-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

1.74 376.0 B 3b.14 2-fluoro-N-isobutyl-N- methyl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.80 346.1 B 3b.15 N-(1,1-dimethyl-3- oxo-butyl)-2-fluoro-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

1.65 374.0 B 3b.16 2-fluoro-N-(2- hydroxybutyly-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.40 348.0 B 3b.17 2-fluoro-N-(3-hydroxy- 1-methyl-propyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.34 348.0 B 3b.18 2-fluoro-N-[1- (hydroxymethyl)-2-methyl-propyl]-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

3b.19 2-fluoro-N-(2- methoxyethyl)-N- methyl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.50 362.0 B 3b.20 N-(4-chlorobutyl)-2- fluoro-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.51 348.1 B 3b.21 2-fluoro-N-(2- hydroxyethyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.70 366.0 B 3b.22 2-fluoro-N-(5- hydroxypentyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.20 319.9 B 3b.23 2-fluoro-N-(3- hydroxypropyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.37 362.0 B 3b.24 N-(3-ethoxypropyl)-2- fluoro-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.25 334.0 B 3b.25 2-fluoro-N-(2- hydroxyethyl)-N- methyl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.64 362.0 B 3b.26 2-fluoro-N-(4- hydroxybutyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.25 334.0 B 3b.27 2-fluoro-N-isopropyl- 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.29 348.0 B 3b.28 ethyl 3-[[2-fluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzoyl]amino] butanoate

1.60 318.1 B 3b.29 2-fluoro-N-(2-hydroxy- 2-methyl-propyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

3b.30 N-allyl-N-ethyl-2- fluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.66 390.0 B 3b.31 2-fluoro-N-hexyl-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.37 348.0 B 3b.32 N,N-diethyl-2-fluoro-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.74 344.1 B 3b.33 N-ethyl-2-fluoro-N-(2- methylallyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.97 360.0 B 3b.34 2-fluoro-N-methyl-N- propyl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.68 332.1 B 3b.35 N-ethyl-2-fluoro-N- isopropyl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.85 358.1 B 3b.36 2-fluoro-N-isopropyl- N-methyl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.69 332.1 B 3b.37 N-tert-butyl-2-fluoro- N-methyl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.78 346.1 B 3b.38 N-butyl-2-fluoro-N- methyl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.67 332.0 B 3b.39 N-(2-ethoxyethyl)-2- fluoro-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.85 346.0 B 3b.40 2-fluoro-N-(2- methoxy-1-methyl- ethyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.81 346.0 B 3b.41 2-fluoro-N-isopentyl- 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.56 348.0 B 3b.42 N-(2-ethylbutyl)-2- fluoro-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.56 348.0 B 3b.43 2-fluoro-N-(2- isopropoxyethyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.84 346.0 B 3b.44 2-fluoro-N-methyl-N- prop-2-ynyl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.95 360.1 B

TABLE T4a Melting point (mp) data and/or retention times (R_(t)) forcompounds according to Formula (I). Mass Table R_(t) charge mp EntryCompound name Structure (mins) (M + H)⁺ Method (°0 C.) 4a.1 N-(p-tolylmethyl)-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3-yl]benzamide

1.09 362.3 A 198-203 4a.2  N-(m-tolylmethyl)-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.09 362.4 A 135-141 4a.3  N-[(4- methoxyphenyl) methyl]-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.04 378.2 A 154-159 4a.4  N-(o-tolylmethyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.08 362.4 A 135-141 4a.5  N-(1-phenylethyl)-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.07 362.3 A 144-148 4a.6  N-(4-chlorophenyl)-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.14 368.2 A 4a.7  N-(2-fluorophenyl)-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.07 352.2 A 4a.8  N-(4-fluorophenyl)-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.08 352.3 A 4a.9  4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl]- N-[3-(trifluoromethyl) phenyl] benzamide

1.17 402.4 A 4a.10 N-(3-ethylphenyl)-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.16 362.4 A 4a.11 N-[(2,5- dimethylphenyl) methyl]-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

B 4a.12 N-(4- morpholinophenyl)-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.62  418.99 B 4a.13 N-[(2,4- dimethoxyphenyl) methyl]-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.7   407.98 B

TABLE T4b Melting point (mp) data and/or retention times (R_(t)) forcompounds according to Formula (I) when R⁴ is R^(4D). Mass Table R_(t)charge mp Entry Compound name Structure (mins) (M + H)⁺ Method (°0 C.)4b.1  2-fluoro-N-[(2- fluorophenyl)methyl]- 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

132-136 4b.2  2-fluoro-N-[(4- fluorophenyl)methyl]-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

145-147 4b.3  2-fluoro-N-(1- phenylethyl)-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

121.1-123.7 4b.4  2-fluoro-N-[(3- fluorophenyl)methyl]-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

129.4-130.9 4b.5  2-fluoro-N-[(2- methoxyphenyl) methyl]-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

113.3-114.8 4b.6  N-benzyl-2-fluoro-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

  146-147.7 4b.7  2-fluoro-N-[2-(4- fluorophenyl)ethyl]-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

128.2-129.4 4b.8  2-fluoro-N-(2- phenylethyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

  130-131.9 4b.9  2-fluoro-N-[(2- fluorophenyl)methyl]- N-methyl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

4b.10 2-fluoro-N-(4- phenylbutyl)-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

4b.11 N-[(3,4- diethoxyphenyl) methyl]-2-fluoro-N- isopropyl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

4b.12 2-fluoro-N-phenyl-4- [5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl]benzamide

4b.13 N-[(3-bromo-4-fluoro- phenyl)methyl]-2- fluoro-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

4b.14 N-[(2,4- dimethoxyphenyl) methyl]-2-fluoro-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

TABLE T5a Melting point (mp) data and/or retention times (R_(t)) forcompounds according to Formula (I). Mass Table R_(t) charge mp EntryCompound name Structure (mins) (M + H)⁺ Method (°0 C.) 5a.1N-(3-cyano-5-methyl-2- thienyl)-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.86 379.1 B 5a.2 N-(3-tert-butyl-1H- pyrazol-5-yl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.68 380.1 B 5a.3 N-(1H-pyrazol-4-yl)-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.29 324 B 5a.4 N-methyl-N-(2-pyridyl)- 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.5 349.1 B 5a.5 N-methyl-N-(1H-1,2,4- triazol-5-yl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.98 339.1 B 125-128 5a.6 N-(3-bromo-1H-1,2,4- triazol-5-yl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

2.07 403.3 B 5a.7 N-[2-(2-thienyl)ethyl]-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.71 368 B 5a.8 N-(1,2,4-triazin-3-yl)-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

2.14 336.9 B 5a.9 N-[(6-chloro-3- pyridyl)methyl]-N- methyl-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.6   396.92 B 5a.10  N-(thiazol-2-ylmethyl)-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.4   354.04 B

TABLE T5b Melting point (mp) data and/or retention times (R_(t)) forcompounds according to Formula (I) when R⁴ is R^(4E). Mass Table R_(t)charge mp Entry Compound name Structure (mins) (M + H)⁺ Method (°0 C.)5b.1  2-fluoro-N-(2- thienylmethyl)-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.06 372.3 A 142.7-143   5b.2  2-fluoro-N-methyl-N-(2-thienylmethyl)-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.08 386.3 A 5b.3  2-fluoro-N-methyl-N-[(3- methyl-2-thienyl)methyl]-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.13 400.4 A 5b.4  N-[[3-chloro-5- (trifluoromethyl)-2-pyridyl]methyl]-2-fluoro- 4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl]benzamide

1.17 469.7 A 126.6-128.3 5b.5  N-[2-[3-chloro-5- (trifluoromethyl)-2-pyridyl]ethyl]-2-fluoro-4- [5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl]benzamide

1.16 483.7 A 144.9-146.5 5b.6  N-(3-tert-butyl-1H-pyrazol-5-yl)-2-fluoro-4- [5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl]benzamide

1.68 398.1 B 5b.7  2-fluoro-N-(1H-pyrazol- 4-yl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.27 342 B 5b.8  2-fluoro-N-(5-methoxy- 1-methyl-1-thia-2,4,6-triazacyclohexa-2,4,6- trien-3-yl)-N-methyl-4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]benzamide

1.61 433.3 B 5b.9  2-fluoro-N-[(5-methyl-2- furyl)methyl]-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.71 370.1 B 5b.10 N-(3-bromo-1H-1,2,4- triazol-5-yl)-2-fluoro-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

1.43 421 B 5b.11 2-fluoro-N-(2- furylmethyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.61 356.1 B 5b.12 2-fluoro-N-(3-imidazol- 1-ylpropyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

0.89 384.1 A 5b.13 2-fluoro-N-[2-(2- thienyl)ethyl]-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.77 386.1 B 5b.14 N-[(2-chlorothiazol-5- yl)methyl]-2-fluoro-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.01 407.7 A 127.8-130.8 5b.15 2-fluoro-N-methyl-N-[(2- methylthiazol-4-yl)methyl]-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

0.99 401.4 A 96.3-98.4 5b.16 2-chloro-N-[(5-methyl-2-furyl)methyl]-4-[5- (trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

0.92 385.94 A 5b.17 2-chloro-N-(2- furylmethyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

0.86 371.92 A 5b.18 2-chloro-N-[2-(2- thienyl)ethyl]-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

0.95 401.92 A 5b.19 2-fluoro-N-(thiazol-2- ylmethyl)-4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3- yl]benzamide

1.44 373.05 B 5b.20 N-[cyano(2- thienyl)methyl]-2-fluoro-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]benzamide

1.06 395 A 138.1-139.2

BIOLOGICAL EXAMPLES General Examples of Leaf Disk Tests in Well Plates

Leaf disks or leaf segments of various plant species are cut from plantsgrown in a greenhouse. The cut leaf disks or segments are placed inmultiwell plates (24-well format) onto water agar. The leaf disks aresprayed with a test solution before (preventative) or after (curative)inoculation. Compounds to be tested are prepared as DMSO solutions (max.10 mg/ml) which are diluted to the appropriate concentration with 0.025%Tween20 just before spraying. The inoculated leaf disks or segments areincubated under defined conditions (temperature, relative humidity,light, etc.) according to the respective test system. A singleevaluation of disease level is carried out 3 to 14 days afterinoculation, depending on the pathosystem. Percent disease controlrelative to the untreated check leaf disks or segments is thencalculated.

General Examples of Liquid Culture Tests in Well Plates

Mycelia fragments or conidia suspensions of a fungus prepared eitherfreshly from liquid cultures of the fungus or from cryogenic storage,are directly mixed into nutrient broth. DMSO solutions of the testcompound (max. 10 mg/ml) are diluted with 0.025% Tween20 by a factor of50 and 10 μl of this solution is pipetted into a microtiter plate(96-well format). The nutrient broth containing the fungalspores/mycelia fragments is then added to give an end concentration ofthe tested compound. The test plates are incubated in the dark at 24° C.and 96% relative humidity. The inhibition of fungal growth is determinedphotometrically after 2 to 7 days, depending on the pathosystem, andpercent antifungal activity relative to the untreated check iscalculated.

Example 1: Fungicidal Activity Against Puccinia recondita f. Sp.Tritici/Wheat/Leaf Disc Preventative (Brown Rust)

Wheat leaf segments cv. Kanzler were placed on agar in multiwell plates(24-well format) and sprayed with the formulated test compound dilutedin water. The leaf disks were inoculated with a spore suspension of thefungus 1 day after application. The inoculated leaf segments wereincubated at 19° C. and 75% relative humidity (rh) under a light regimeof 12 hours light/12 hours darkness in a climate cabinet and theactivity of a compound was assessed as percent disease control comparedto untreated when an appropriate level of disease damage appears inuntreated check leaf segments (7 to 9 days after application).

The following compounds at 200 ppm in the applied formulation give atleast 80% disease control in this test when compared to untreatedcontrol leaf disks under the same conditions, which show extensivedisease development.

Compounds (from Table T1a) 1a.1, 1a.2, 1a.3, 1a.4, 1a.6, 1a.7, 1a.10,and 1a.11

Compounds (from Table T1b) 1b.1, 1b.2, 1b.3, 1b.4, 1b.5, 1b.6, 1b.8,1b.9, 1b.11, 1b.13, 1b.14, 1b.15, 1b.16, 1b.17, and 1b.18.

Compounds (from Table T2a) 2a.3, 2a.4, 2a.6, 2a.7, and 2a.9.

Compounds (from Table T2b) 2b.1, 2b.3, 2b.4, 2b.5, 2b.9, 2b.10, 2b.11,2b.12, 2b.13, 2b.14, 2b.15, 2b.16, and 2b.17.

Compounds (from Table T3a) 3a.1, 3a.2, 3a.3, 3a.4, 3a.5, 3a.7, 3a.9,3a.10, 3a.11, 3a.12, 3a.13, 3a.14, 3a.16, 3a.17, 3a.20, 3a.22, 3a.24,3a.26, 3a.27, 3a.28, 3a.30, 3a.31, 3a.32, 3a.33, 3a.34, 3a.35, 3a.36,3a.37, 3a.38, 3a.40, 3a.41, 3a.43, 3a.44, and 3a.45.

Compounds (from Table T3b) 3b.1, 3b.2, 3b.3, 3b.4, 3b.5, 3b.6, 3b.7,3b.8, 3b.10, 3b.11, 3b.12, 3b.14, 3b.15, 3b.16, 3b.19, 3b.20, 3b.21,3b.22, 3b.24, 3b.26, 3b.27, 3b.28, 3b.29, 3b.30, 3b.32, 3b.33, 3b.34,3b.35, 3b.36, 3b.37, 3b.38, 3b.39, 3b.40, 3b.41, 3b.43, and 3b.44.

Compounds (from Table T4a) 4a.2, 4a.3, 4a.4, 4a.5, and 4a.13.

Compounds (from Table T4b) 4b.1, 4b.2, 4b.3, 4b.4, 4b.5, 4b.6, 4b.7,4b.8, 4b.9, 4b.11, 4b.13, and 4b.14.

Compounds (from Table T5a) 5a.5, 5a.6, 5a.7, 5a.8, 5a.9, and 5a.10.

Compounds (from Table T5b) 5b.1, 5b.2, 5b.7, 5b.9, 5b.10, 5b.11, 5b.13,5b.14, 5b.15, 5b.16, 5b.17, 5b.18, 5b.19, and 5b.20.

Example 2: Fungicidal Activity Against Puccinia recondita f. Sp.Tritici/Wheat/Leaf Disc Curative (Brown Rust)

Wheat leaf segments cv. Kanzler are placed on agar in multiwell plates(24-well format). The leaf segments are then inoculated with a sporesuspension of the fungus. Plates were stored in darkness at 19° C. and75% relative humidity. The formulated test compound diluted in water wasapplied 1 day after inoculation. The leaf segments were incubated at 19°C. and 75% relative humidity under a light regime of 12 hours light/12hours darkness in a climate cabinet and the activity of a compound wasassessed as percent disease control compared to untreated when anappropriate level of disease damage appears in untreated check leafsegments (6 to 8 days after application).

The following compounds at 200 ppm in the applied formulation give atleast 80% disease control in this test when compared to untreatedcontrol leaf disks under the same conditions, which show extensivedisease development.

Compounds (from Table T1a) 1a.2, 1a.3, 1a.4, 1a.5, 1a.7, 1a.8, and 1a.9.

Compounds (from Table T1b) 1b.2, 1b.5, 1b.6, 1b.7, 1b.9, 1b.10, 1b.12,1b.13, 1b.15, 1b.16, 1b.17, and 1b.18.

Compounds (from Table T2a) 2a.3, 2a.4, and 2a.9.

Compounds (from Table T2b) 2b.1, 2b.3, 2b.4, 2b.5, 2b.9, 2b.11, 2b.12,2b.13, and 2b.17.

Compounds (from Table T3a) 3a.1, 3a.2, 3a.3, 3a.5, 3a.6, 3a.7, 3a.9,3a.10, 3a.11, 3a.12, 3a.13, 3a.14, 3a.15, 3a.16, 3a.17, 3a.18, 3a.20,3a.21, 3a.22, 3a.24, 3a.27, 3a.28, 3a.30, 3a.31, 3a.32, 3a.33, 3a.34,3a.35, 3a.36, 3a.37, 3a.38, 3a.40, 3a.41, 3a.43, 3a.44, and 3a.45.

Compounds (from Table T3b) 3b.1, 3b.2, 3b.3, 3b.4, 3b.5, 3b.6, 3b.8,3b.9, 3b.10, 3b.11, 3b.12, 3b.14, 3b.15, 3b.16, 3b.17, 3b.18, 3b.19,3b.20, 3b.21, 3b.22, 3b.23, 3b.24, 3b.27, 3b.28, 3b.29, 3b.30, 3b.31,3b.32, 3b.33, 3b.34, 3b.35, 3b.36, 3b.37, 3b.38, 3b.39, 3b.40, 3b.41,3b.43, and 3b.44.

Compounds (from Table T4a) 4a.4, 4a.5, and 4a.13.

Compounds (from Table T4b) 4b.6, and 4b.9.

Compounds (from Table T5a) 5a.4, 5a.5, 5a.6, 5a.8, 5a.9, and 5a.10.

Compounds (from Table T5b) 5b.1, 5b.2, 5b.3, 5b.9, 5b.11, 5b.13, 5b.14,5b.15, 5b.16, 5b.17, 5b.19, and 5b.20.

Example 3: Fungicidal Activity Against Phakopsorapachyrhizi/Soybean/Leaf Disc Preventative (Asian Soybean Rust)

Soybean leaf disks are placed on water agar in multiwell plates (24-wellformat) and sprayed with the formulated test compound diluted in water.One day after application leaf discs are inoculated by spraying a sporesuspension on the lower leaf surface. After an incubation period in aclimate cabinet of 24-36 hours in darkness at 20° C. and 75% rh leafdisc are kept at 20° C. with 12 h light/day and 75% rh. The activity ofa compound is assessed as percent disease control compared to untreatedwhen an appropriate level of disease damage appears in untreated checkleaf disks (12 to 14 days after application).

The following compounds at 200 ppm in the applied formulation give atleast 80% disease control in this test when compared to untreatedcontrol leaf disks under the same conditions, which show extensivedisease development.

Compounds (from Table T1a) 1a.1 and 1a.2.

Compounds (from Table T1b) 1b.1, 1b.2, 1b.3, 1b.5, 1b.6, 1b.9, 1b.14,1b.15, 1b.16, 1b.17, and 1b.18.

Compounds (from Table T2a) 2a.1, 2a.2, 2a.3, 2a.4, 2a.5, 2a.6, 2a.7,2a.8, and 2a.9

Compounds (from Table T2b) 2b.1, 2b.2, 2b.3, 2b.4, 2b.5, 2b.6, 2b.7,2b.8, 2b.9, 2b.11, 2b.12, 2b.13, 2b.15, and 2b.17.

Compounds (from Table T3a) 3a.1, 3a.2, 3a.3, 3a.4, 3a.5, 3a.6, 3a.7,3a.8, 3a.9, 3a.10, 3a.11, 3a.12, 3a.13, 3a.14, 3a.15, 3a.16, 3a.18,3a.19, 3a.20, 3a.21, 3a.22, 3a.23, 3a.24, 3a.25, 3a.26, 3a.27, 3a.28,3a.29, 3a.30, 3a.31, 3a.32, 3a.33, 3a.34, 3a.35, 3a.36, 3a.37, 3a.38,3a.39, 3a.40, 3a.41, 3a.42, 3a.43, 3a.44, and 3a.45.

Compounds (from Table T3b) 3b.1, 3b.2, 3b.3, 3b.4, 3b.5, 3b.6, 3b.7,3b.8, 3b.9, 3b.10, 3b.11, 3b.12, 3b.13, 3b.14, 3b.15, 3b.16, 3b.17,3b.19, 3b.20, 3b.21, 3b.22, 3b.23, 3b.24, 3b.25, 3b.26, 3b.27, 3b.29,3b.30, 3b.31, 3b.32, 3b.33, 3b.34, 3b.35, 3b.36, 3b.37, 3b.38, 3b.39,3b.40, 3b.41, 3b.42, 3b.43, and 3b.44.

Compounds (from Table T4a) 4a.1, 4a.2, 4a.3, 4a.4, 4a.5, 4a.6, 4a.7,4a.8, 4a.9, 4a.10, 4a.11, 4a.12, 4a.13.

Compounds (from Table T4b) 4b.1, 4b.2, 4b.3, 4b.4, 4b.5, 4b.6, 4b.7,4b.8, 4b.9, 4b.10, and 4b.12.

Compounds (from Table T5a) 5a.1, 5a.2, 5a.3, 5a.4, 5a.5, 5a.6, 5a.7,5a.8, 5a.9, and 5a.10.

Compounds (from Table T5b) 5b.1, 5b.2, 5b.3, 5b.4, 5b.5, 5b.6, 5b.7,5b.8, 5b.9, 5b.11, 5b.12, 5b.13, 5b.14, 5b.15, 5b.16, 5b.17, 5b.19, and5b.20.

Example 4: Fungicidal Activity Against Glomerella Lacenarium(Colletotrichum Lacenarium) Liquid Culture/Cucumber/Preventative(Anthracnose)

Conidia of the fungus from cryogenic storage are directly mixed intonutrient broth (PDB-potato dextrose broth). After placing a (DMSO)solution of test compound into a microtiter plate (96-well format), thenutrient broth containing the fungal spores is added. The test platesare incubated at 24° C. and the inhibition of growth is measuredphotometrically 3 to 4 days after application.

The following compounds at 20 ppm in the applied formulation give atleast 80% disease control in this test when compared to untreatedcontrol under the same conditions, which show extensive diseasedevelopment.

Compounds (from Table T1a) 1a 1, 1a.2, 1a.3, 1a.4, and 1a.5.

Compounds (from Table T1b) 1b.5, 1b.9, 1b.14, 1b.15, 1b.16, 1b.17, and1b.18.

Compounds (from Table T2a) 2a.1 and 2a.9.

Compounds (from Table T2b) 2b.1, 2b.2, 2b.3, 2b.4, 2b.5, 2b.6, 2b.8, and2b.13.

Compounds (from Table T3a) 3a.1, 3a.2, 3a.3, 3a.4, 3a.7, 3a.8, 3a.9,3a.10, 3a.11, 3a.12, 3a.13, 3a.14, 3a.16, 3a.17, 3a.18, 3a.20, 3a.22,3a.23, 3a.24, 3a.25, 3a.26, 3a.27, 3a.28, 3a.29, 3a.30, 3a.31, 3a.32,3a.33, 3a.34, 3a.35, 3a.36, 3a.37, 3a.38, 3a.39, 3a.40, 3a.41, 3a.43,3a.44, and 3a.45.

Compounds (from Table T3b) 3b.1, 3b.2, 3b.3, 3b.4, 3b.5, 3b.6, 3b.7,3b.8, 3b.10, 3b.11, 3b.12, 3b.13, 3b.14, 3b.15, 3b.16, 3b.18, 3b.19,3b.20, 3b.21, 3b.22, 3b.23, 3b.24, 3b.26, 3b.27, 3b.28, 3b.29, 3b.30,3b.31, 3b.32, 3b.33, 3b.34, 3b.35, 3b.36, 3b.37, 3b.38, 3b.39, 3b.40,3b.41, 3b.43, and 3b.44.

Compounds (from Table T4a) 4a.1, 4a.2, 4a.3, 4a.4, 4a.5, and 4a.13.

Compounds (from Table T4b) 4b.1, 4b.2, 4b.5, 4b.7, 4b.8, 4b.9, 4b.10,and 4b.11.

Compounds (from Table T5a) 5a.4, 5a.5, 5a.6, 5a.7, 5a.8, 5a.9, and5a.10.

Compounds (from Table T5b) 5b.2, 5b.3, 5b.7, 5b.9, 5b.10, 5b.11, 5b.13,5b.14, 5b.15, 5b.16, 5b.17, 5b.18, 5b.19, and 5b.20.

Example 5: Fungicidal Activity Against Uromyces viciae-Fabael FieldBean/Leaf Disc Preventative (Faba-Bean Rust)

Field bean leaf discs are placed on water agar in multiwell plates(96-well format) and 10 μl of the formulated test compound diluted inacetone and a spreader pipetted onto the leaf disc. Two hours afterapplication leaf discs are inoculated by spraying a spore suspension onthe lower leaf surface. The leaf discs are incubated in a climatecabinet at 22° C. with 18 hour day and 70% relative humidity. Theactivity of a compound is assessed as percent disease control comparedto untreated when an appropriate level of disease damage appears inuntreated check leaf disks (12 days after application).

The following compounds at 100 ppm in the applied formulation give atleast 80% disease control in this test when compared to untreatedcontrol leaf discs under the same conditions, which show extensivedisease development.

Compounds (from Table T1a) 1a.2, 1a.3, 1a.4, 1a.5, 1a.6, 1a.7, 1a.8,1a.9, 1a.10, and 1a.11.

Compounds (from Table T1b) 1b.1, 1b.2, 1b.3, 1b.4, 1b.5, 1b.6, 1b.7,1b.8, 1b.9, 1b.10, 1b.11, 1b.12, 1b.13, 1b.14, 1b.15, 1b.16, 1b.17, and1b.18.

Compounds (from Table T2a) 2a.2, 2a.3, 2a.4, 2a.5, 2a.6, 2a.7, 2a.8,2a.9.

Compounds (from Table T2b) 2b.1, 2b.2, 2b.3, 2b.4, 2b.5, 2b.6, 2b.7,2b.8, 2b.10, 2b.11, 2b.12, 2b.14, 2b.15, 2b.16, and 2b.17.

Compounds (from Table T3a) 3a.1, 3a.2, 3a.3, 3a.4, 3a.5, and 3a.17.

Compounds (from Table T3b) 3b.1, 3b.2, 3b.3, 3b.4, 3b.5, 3b.6, 3b.7, and3b.8.

Compounds (from Table T4a) 4a.1, 4a.2, 4a.3, 4a.4, 4a.5, 4a.6, 4a.7,4a.8, 4a.9, 4a.10, 4a.11, 4a.12, and 4a.13.

Compounds (from Table T4b) 4b.1, 4b.2, 4b.3, 4b.4, 4b.5, 4b.6, 4b.7,4b.8, 4b.9, 4b.10, 4b.11, 4b.12, 4b.13, and 4b.14.

Compounds (from Table T5a) 5a.2, 5a.5, 5a.7, 5a.9, and 5a.10.

Compounds (from Table T5b) 5b.1, 5b.2, 5b.3, 5b.4, 5b.5, 5b.6, 5b.7,5b.9, 5b.10, 5b.11, 5b.12, 5b.13, 5b.14, 5b.15, 5b.16, 5b.17, 5b.18,5b.19, and 5b.20.

The invention claimed is:
 1. A method of controlling or preventinginfestation of useful plants by phytopathogenic microorganisms,comprising applying to the plants, to parts thereof or the locus thereofa fungicidally effective amount of a compound of formula (I):

wherein R¹ is hydrogen; R² is halogen, methyl or methoxy; R³ representshydrogen or C₁₋₄alkyl; and R⁴ represents R^(4A), R^(4B), R^(4C), R^(4D)or R^(4E); wherein R^(4A) represents heterocyclylC₀₋₆alkyl wherein theheterocyclyl moiety is a 5- or 6-membered non-aromatic ring whichcomprises 1, 2 or 3 heteroatoms individually selected from N, O and S,optionally substituted by 1, 2 or 3 substituents, which may be the sameor different, selected from R^(5A); R^(5A) represents C₁₋₄alkyl,C₁₋₄alkoxy, C₁₋₄alkoxycarbonyl, phenylC₀₋₂alkyl; R^(4B) representsC₃₋₈cycloalkylC₀₋₆alkyl optionally substituted by 1, 2, 3 or 4substituents, which may be the same or different, selected from R^(5B);R^(5B) represents cyano, halogen, C₁₋₄alkyl, C₂₋₄alkynyl,C₁₋₄alkoxycarbonyl, C₃₋₆cycloalkylC₀₋₂alkyl, phenylC₀₋₂alkyl, andwherein any of said cycloalkyl or phenyl moieties are optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R^(6B); and R^(6B) represents methyl, methoxyor halogen; R^(4C) represents C₁₋₆alkyl, C₂₋₆alkenyl or C₂₋₆alkynyl,wherein C₁₋₆alkyl is optionally substituted by 1, 2 or 3 substituents,which may be the same or different, selected from R^(5C); R^(5C)represents halogen, C₁₋₄alkoxy, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl,hydroxyl, C₁₋₄alkylaminocarbonyl; R^(4D) represents a phenylC₀₋₆alkyloptionally substituted by 1, 2, 3, 4 or 5 substituents, which may be thesame or different, selected from R^(5D); R^(5D) represents cyano,halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl, C₂₋₄alkynyl, haloC₁₋₄alkyl,C₁₋₄alkoxy, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, aminocarbonyl,C₁₋₄alkylaminocarbonyl, diC₁₋₄alkylaminocarbonyl,C₁₋₄alkoxycarbonylamino, C₃₋₈cycloalkylC₀₋₆alkyl, phenylC₀₋₆alkyl,heteroarylC₀₋₆alkyl wherein the heteroaryl moiety is a 5- or 6-memberedaromatic ring which comprises 1, 2, 3 or 4 heteroatoms individuallyselected from N, O and S, heterocyclylC₀₋₆alkyl wherein the heterocyclylmoiety is a 5- or 6-membered non-aromatic ring which comprises 1, 2 or 3heteroatoms individually selected from N, O and S, and wherein any ofsaid cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties areoptionally substituted by 1, 2, 3, 4 or 5 substituents, which may be thesame or different, selected from R^(6D); and R^(6D) represents methyl,methoxy or halogen; and R^(4E) represents heteroarylC₀₋₆alkyl whereinthe heteroaryl moiety is a 5- or 6-membered aromatic ring comprising 1,2, 3 or 4 heteroatoms individually selected from N, O and S, and whereinthe heteroarylC₀₋₆alkyl moiety is optionally substituted by 1, 2, 3, 4or 5 substituents, which may be the same or different, selected fromR^(5E); R^(5E) represents cyano, amino, halogen, hydroxy, C₁₋₄alkyl,C₂₋₄alkenyl, C₂₋₄alkynyl, haloC₁₋₄alkyl, C₁₋₄alkoxy, C₁₋₄alkylamino,diC₁₋₄alkylamino, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, aminocarbonyl,C₁₋₄alkylaminocarbonyl, diC₁₋₄alkylaminocarbonyl,C₁₋₄alkoxycarbonylamino, C₃₋₈cycloalkylC₀₋₆alkyl, phenylC₀₋₆alkyl,heteroarylC₀₋₆alkyl wherein the heteroaryl moiety is a 5- or 6-memberedaromatic ring which comprises 1, 2, 3 or 4 heteroatoms individuallyselected from N, O and S, heterocyclylC₀₋₆alkyl wherein the heterocyclylmoiety is a 5- or 6-membered non-aromatic ring which comprises 1, 2 or 3heteroatoms individually selected from N, O and S, and wherein any ofsaid cycloalkyl, phenyl, heteroaryl and heterocyclyl are optionallysubstituted by 1, 2, 3, 4 or 5 substituents, which may be the same ordifferent, selected from R^(6E); and R^(6E) represents methyl, methoxyor halogen; or a salt or an N-oxide thereof, or a composition comprisingthe compound of formula (I) as an active ingredient.
 2. The method ofclaim 1, wherein when R⁴ is R^(4A), the compound according to Formula(I) is not:2-fluoro-N-(pyrrolidin-3-yl)-4-[(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)]benzamide,2-fluoro-N-(1-(pyrrolidin-1-yl)propan-2-yl)-4-[(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)]benzamide,2-fluoro-N-(1-(piperidin-1-yl)propan-2-yl)-4-[(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)]benzamide,2-fluoro-N-(1-morpholinopropan-2-yl)-4-[(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)]benzamide,or2-fluoro-N-(4-methoxypyrrolidin-3-yl)-4-[(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)]benzamide;when R⁴ is R^(4C), the compound according to Formula (I) is not:2-fluoro-N-(1-hydroxypropan-2-yl)-4-[(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)]benzamide;and when R⁴ is R^(4E), the compound according to Formula (I) is not:N-(2,6-dimethylpyridin-4-yl)-2-fluoro-4-(5-(trifluoromethyl)-)-1,2,4-oxadiazol-3-yl)benzamide.3. The method of claim 2, wherein R² is halogen.
 4. The method of claim2, wherein R³ is hydrogen or methyl.
 5. The method of claim 2, whereinR⁴ is R^(4A) and R^(4A) represents heterocyclylC₀₋₂alkyl wherein theheterocyclyl moiety is a 5- or 6-membered non-aromatic ring whichcomprises 1, 2 or 3 heteroatoms individually selected from N, O and S,and wherein the heterocyclylC₀₋₂alkyl moiety is optionally substitutedby 1 or 2 substituents, which may be the same or different, selectedfrom R^(5A).
 6. The method of claim 5, wherein R^(5A) represents methyl,methoxy, methoxycarbonyl, tert-butyloyxcarbonyl or benzyl.
 7. The methodof claim 2, wherein R⁴ is R^(4B) and R^(4B) representsC₃₋₆cycloalkylC₀₋₂alkyl optionally substituted by 1 or 2 substituents,which may be the same or different, selected from R^(5B).
 8. The methodof claim 2, wherein R⁴ is R^(4C) and R^(4C) represents: (i) C₁₋₆alkyl;(ii) C₁₋₆alkyl substituted by a single substituent selected from R^(5C),wherein R^(5C) represents C₁₋₄alkoxy or hydroxyl; or (iii) C₂₋₆alkenylor C₂₋₆alkynyl, preferably C₂₋₆alkynyl.
 9. The method of claim 2,wherein R⁴ is R^(4D) and R^(4D) represents phenylC₀₋₂alkyl optionallysubstituted by 1 or 2 substituents, which may be the same or different,selected from R^(5D).
 10. The method of claim 9, wherein R^(5D)represents cyano, halogen, C₁₋₄alkyl, haloC₁₋₂alkyl, C₁₋₂alkoxy,aminocarbonyl, each optionally substituted by 1, 2 or 3 substituents,which may be the same or different, selected from R^(6D).
 11. The methodof claim 2, wherein R⁴ is R^(4E) and R^(4E) representsheteroarylC₀₋₂alkyl, wherein the heteroaryl is a 5-membered ringcomprising 1 or 2 heteroatoms individually selected from N, O and S, andwherein the heteroarylC₀₋₂alkyl is optionally substituted by 1 or 2substituents, which may be the same or different, selected from R^(5E).12. The method of claim 11, wherein R^(5E) represents amino, cyano,halogen, C₁₋₄alkyl, haloC₁₋₂alkyl or C₁₋₂alkoxy.
 13. The method of claim2, wherein when R² is F, R³ is H, R⁴ is not substituted or unsubstituted1-(pyrrolidin-1-yl)propan-2-yl; when R² is F, R³ is H, R⁴ is notsubstituted or unsubstituted pyrrolidin-3-yl; when R² is F, R³ is H, R⁴is not substituted or unsubstituted 1-(piperidin-1-yl)propan-2-yl; whenR² is F, R³ is H, R⁴ is not substituted or unsubstituted1-morpholinopropan-2-yl; when R² is F, R³ is H, R⁴ is not substituted orunsubstituted 4-methoxypyrrolidin-3-yl; when R² is F, R³ is H, R⁴ is notsubstituted or unsubstituted 1-hydroxypropan-2-yl; and when R² is F, R³is H, R⁴ is not substituted or unsubstituted 2,6-dimethylpyridin-4-yl.14. The method of claim 2, wherein when R² is F, R³ is H, R⁴ is notR^(4A) wherein R^(4A) is a C₀₋₆alkyl 5- or 6-membered non-aromaticheterocyclyl moiety comprising 1 heteroatom selected from N andoptionally substituted by 1 substituents selected from R^(5A); when R²is F, R³ is H, R⁴ is not R^(4A) wherein R^(4A) is a C₀₋₆alkyl 6-memberednon-aromatic heterocyclyl moiety comprising 2 heteroatom one being N andthe other being O and optionally substituted by 1 substituents selectedfrom R^(5A); when R² is F, R³ is H, R⁴ is not R^(4C) wherein R^(4C) is aC₁₋₆alkyl optionally substituted by 1 substituents selected from R^(5C);and when R² is F, R³ is H, R⁴ is not R^(4E) wherein R^(4E) is aC₀₋₆alkyl 6-membered heteroaryl moiety comprising 1 heteroatom selectedfrom N and optionally substituted by 1, 2, 3, or 4 substituents selectedfrom R^(5E) wherein R^(5E) is C₁₋₄alkyl.
 15. The method of claim 2,wherein R⁴ is R^(4B).
 16. The method of claim 2, wherein R⁴ is R^(4D).17. The method of claim 2, wherein R² is F.